(3.237.97.64) 您好!臺灣時間:2021/03/03 04:35
字體大小: 字級放大   字級縮小   預設字形  
回查詢結果

詳目顯示:::

我願授權國圖
: 
twitterline
研究生:亞洛克
研究生(外文):Arockiya Samy Abragam Joseph
論文名稱:1,1,1,3,3,3-Hexamethyldisilazane (HMDS) Trimethylsilylation of Alcohols for Concise Carbohydrate Synthesis
指導教授:林俊成林俊成引用關係王正中王正中引用關係
指導教授(外文):Lin, Chun-ChengWang, Cheng-Chung
學位類別:博士
校院名稱:國立清華大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2015
畢業學年度:103
語文別:英文
論文頁數:343
中文關鍵詞:六甲基二矽氮烷矽烷基化反應磷酸化反應不對稱化海藻醣
外文關鍵詞:HMDSSilylationPhosphorylationTrehalose desymmetrization
相關次數:
  • 被引用被引用:0
  • 點閱點閱:192
  • 評分評分:系統版面圖檔系統版面圖檔系統版面圖檔系統版面圖檔系統版面圖檔
  • 下載下載:18
  • 收藏至我的研究室書目清單書目收藏:0
本論文致力於開發一系列具位置選擇性之保護與官能基化的一鍋化合成策略,特別是,-海藻醣的衍生醣脂質。在第一章裡,我們利用三甲矽烷基三氟甲磺酸酯 (TMSOTf) 催化六甲基二矽氮烷 (HMDS) 有效地使醣類完全矽烷基化以利下一步反應,並在沒有酵素試劑的幫助下,對未保護的醣類進行選擇性醋酸化反應。結合此簡單的矽烷基化反應,我們成功於兩步內合成出許多高產率之6-磷酸化碳水化合物,也驚訝地觀察到具位置選擇性之雙醣單磷酸化反應。其中,由於6-磷酸化海藻醣於生物學上、對植物生長的重要性而受到注目。不同於其它醣類,海藻醣為一對稱分子。然而,許多與結核菌毒性有關的海藻醣衍生醣脂質主要為非對稱結構。利用此選擇性磷酸化反應,我們能有效地合成不對稱之海藻醣。

在第二章中,我們也開發了高效率的乙腈催化六甲基二矽氮烷之三甲矽烷基化合成方法,此具有化學選擇性的方法可將羥基三甲矽烷基化並留下氨基,以利接下來對氨基醣之氮原子進行勻相、具化學選擇性的官能基化反應。此合成方法不僅能夠應用在如葡萄糖胺、半乳醣胺、唾液酸等結構單純的氨基醣基質,也適用於結構複雜的氨基醣基質,如新黴素硫酸化物與其它氨基醣分子。應用於6-磷酸化葡萄醣胺的化學合成方法有效地達到在極短的步驟內獲得極佳的總產率。


This thesis is concern with regioselective one-pot protections and functionalisations of carbohydrates, especially on ,-trehalose-derived glycolipids. In chapter 1, we developed an efficient TMSOTf-catalyzed-HMDS silylation of sugars which can easily lead to subsequent reactions in a one-pot fashion and selective non-enzymatic acetylation reactions directly from unprotected sugar. By incorporating this simple silylation method we synthesized many carbohydrate 6-phosphates easily in 2 steps in excellent yields, and surprisingly we also observed the regioselective mono phosphorylation in disaccharides as well. Among them trehalose 6-phosphate was highlighted, because of its biological importance in plant growth. Apart from that, trehalose is a symmetrical molecule, however, many trehalose based glycolipids are involved in virulence of mycobacterium tuberculosis, but they are majorly unsymmetrical. By utilizing our selective phosphorylation method, we are able to desymmetrize trehalose effectively in chapter 2.
In chapter 3, we describe a highly efficient CH3CN-promoted HMDS trimethylsilylation method that chemoselectively trisilylates hydroxyl groups over the amine groups and enable the subsequent homogenous chemoselective N-functionalisation of amino sugars. This method can not only be applied to simple amino sugar substrates, such as glucosamine, mannosamine, galactosamine and sialic acid, but also multiple amine substrates, like neomycin trisulfate and other amino glycosides. The application to the chemical synthesis of glucosamine 6-phosphate was efficiently achieved in an excellent overall yield in very short steps.

Abstract ..................…………………………………………………………………………....i
摘要………………………………………………………………....…………….....................ii
Acknowledgements………………………………...........…………………………………………..iii
Abbreviations.............................................iv
Content...................................................ix
1. Chapter1. Regioselective Phosphorylation of Carbohydrates via the Per-O-trimethylsilylated Sugars
1.1: Introduction of Carbohydrates………………………………………………….....1
1.2: Phosphorylated carbohydrates in nature ...............2
1.2.1: Glucose 6-phosphate (Robinson ester)............3
1.2.2: Mannose 6-phosphate (Man-6-P)………………..…………...4
1.3. Synthesis of carbohydrate phosphate esters...4
1.3.1. Enzymatic synthesis.............4
1.3.2. Chemo enzymatic Synthesis…….....5
1.3.3. Chemical synthesis………….........…6
1.3.3.1. Metal Catalyzed Phosphorylation of Sugars.....................................................6
1.3.3.2. Solid phase reagent for regioselective monophosphorylation………......................7
1.3.3.3. Silyl ether mediated phosphorylation……………………………...........................….....8
1.4. Trimethylsilyl ethers (TMS)………….........…8
1.4.1. Importance of TMS protection in carbohydrates…………………….....................................…9
1.4.2. Regioselective 6-Detrimethylsilylation of carbohydrates……………...….................................12
1.4.3. Classical silylation methods……………………………………………................................….12
1.4.4. HMDS as a silylating reagent……………………………………………...13
1.4.5 Solvent promoted HMDS silylation of alcohols…………………………....14
1.5. Specific Aims…………………………………………………………………….16
1.6. Result and Discussion……………………………………………………………17
1.7. Regioselective phosphorylation………………………………………………….24
1.7.1 One-pot regioselective 06 phosphorylation of monosaccharides…………...25
1.7.2. Hydrogenolysis of sugar phosphates……………………………………….30
1.8. Trehalose 6-phosphate (Tre-6-P)…………………………………………………32
1.8.1 Trehalose-6-phosphate metabolism in plants……………………………….32
1.8.2. Sucrose-6’-phoaphate……………………………………………………..34
1.8.3. Lactose-6-phosphate……………………………………………………34
1.9. Chemical synthesis of Trehalose 6-phosphate……………………………………..35
1.9.1. Direct phosphorylation of Trehalose…………………………………………35
1.9.2. Silyl group mediated phosphorylation of trehalose…………………………..36
1.10. One-pot regioselective 06 phosphorylation of Disaccharides………………..37
1.11. Conclusions………………………………………………………………………..48
1.12 References………………………………………………………………………….50
2. Chapter 2 : Desymmetrization of Trehalose via Regioselective mono phosphorylation..59
2.1. Trehalose-derived glycolipids…………………………………………………....59
2.2. Analogues of trehalose…………………………………………………………......60
2.2.1. Synthesis from glucose………………………………………………………60
2.2.2. Synthesis from trehalose……………………………………………………..62
2.3. Specific Aim: Desymmetrization of trehalose………………………………….....66
2.3.1. Dephosphorylation reaction………………………………………………….66
2.4. Result and Discussion…………………………………………….............................67
2.5. Conclusions…………………………………………………………………………69
2.6. References…………………………………………………………………………..70

Chapter 3: Chemoselective Per-O-trimethylsilylation and Homogeneous N-functionalisation of Amino Sugars.
3.1. Introduction of aminosugars…………………………………………....................…72
3.2. Amino sugars in tumours………………………………………........................…….73
3.3. Importance of amine protecting groups in amino sugar-containing oligosaccharide Synthesis…………………………………………………………………………………74
3.4. Schotten-Baumann Condition………………………………………………………76
3.5. Recent applications of silyl protecting groups in amino sugars………...........................77
3.5.1. Regioselective one-pot protection of the D-glucosamine……………...……….77
3.5.2. Streamlined regioselective one-pot protection of the D-glucosamine
Derivative...................................................................................................................78
3.5.3. Selective one-pot transformation of D-glucosamine derivatives………..........……78
3.5.4. Microwave-Assisted One-pot synthesis of 1,6-Anhydrosugars of Glucosamine
Derivatives……………………………………………………………………..79
3.5.5. Reported applications of per-O-trimethylsilylated glucosamine…………......……80
3.6. Silylation of amino sugars…………………………………………………………….81
3.7. Result and discussion for homogeneous N-functionalisation…………………………83
3.8. Diazotransfer reaction…………………………………………………………………86
3.9. Chemoselective amine functionalization of sialic acid derivative…………………….88
3.10. Chemoselective per-O-trimethylsilylation and amine functionalization of
Neomycin sulphate…………………………………………………………………...88
3.11. Role of glucosamine-6-phosphate…………………………………………………….89
3.12. Synthesis of glucosamine-6-phosphate……………………………………………….91
3.12.1. Chemical synthesis……………………………………………………………91
3.12.2. Enzymatic synthesis…………………………………………………………..92
3.13. Our concise synthesis of glucosamine-6-phosphate……………………………..93
3.14. Conclusion……………………………………………………………………….96
3.15. References…………………………………………………………………………….97
4. Experimental section..............................................................................................................101
5. Appendix
5.1. NMR Spectra.................................................................................................................151
5.2. Papers.................................................................................................................................328

Chapter-1
1. Varki, A.; Cummings, D. R.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E. Essentials of Glycobiology, 2nd edition. Cold Spring Harbor, New York. 2008.
2. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. Zachara, N. E.; Hart, G. W. Chem. Rev. 2002, 102, 431-438.
4. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357-2364.
5. Parekh, R. B.; Rohhlf, C. Curr. Opin. Biotech. 1997, 8, 718-723.
6. Rudd, P. M.; Joao, H. C.; Coghill, E.; Fiten, P.; Saunders, M. R.; Opdenakker, G.; Dwek, R. A. Biochemistry 1994, 33, 17-22.
7. Parodi, A. J. Annu. Rev. Biochem. 2000, 69, 69-93.
8. Ohtsubo, K.; Marth, J.D. Cell 2006, 126, 855-867.
9. Mitra, N.; Sinha, S.; Ramia, T. N; Surolia, A. Trends Biochem. Sci. 2006, 31, 156-163.
10. Apweiler, R.; Hermjakop, H.; Sharon, N. Biocchim. Biophys. Acta. 1999, 1473, 4-8.
11. Lowe, J. B. Cell. 2001, 104, 809-812.
12. Kansas, G. S. Blood. 1996, 88, 3259-3279.
13. Danishefsky, S. J.; Allen, J. R. Angew. Chem. Int. Ed. 2000, 39, 836-863.
14. Mrksich, M. Chem. Biol. 2004, 11, 739-747.
15. Shriver, Z.; Raguram, S.; Sasisekaran, R. Nature Methods 2005, 2, 817-824.
16. Coullerez, G.; Seeberger, P. H.; Textor, M. Macromol. Biosci. 2006, 6, 634-647.
17. Feizi, T.; Mulloy, B. Curr. Opin. Struc. Biol. 2003, 13, 602-604.
18. Khersonsky, S. M.; Ho, C. M.; Garcia, M. F.; Chang, Y.T. Curr. Topic. Med. Chem. 2003, 3, 617-643.
19. Timmer, M. SM.; Stocker, B. L.; Seeberger, P. H. Curr. Opin. Chem. Biol. 2007, 11, 59-65.
20. Westheimer, F. H. Science 1987, 235, 1173–1178.
21. Bowler, M. W.; Cliff, M. J.; Waltho, J. P.; Blackburn, G. M. New J. Chem. 2010, 34, 784-794.
22. (a) Neufeld, E. F.; Ginsburg, V. Annu. Rev. Biochem. 1965, 34, 297-312. (b) Thompson, J.; Gentry-Weeks, C. R.; Nguyen, N. Y.; Folk, J. E.; Robrish, S. A. J. Bacteriol. 1995, 177, 2505-2512. (c) Bouma, C. L.; Reizer, J.; Reizer, A.; Robrish, S. A.; Thompson, J. J. Bacteriol. 1997, 179, 4129-4137. (d) Thompson, J.; Pikis, A.; Ruvinov, S. B.; Henrissat, B.; Yamamoto, H.; Sekiguchi, J. J. Biol. Chem. 1998, 273, 27347-27356. (e) Thompson, J.; Ruvinov, S. B.; Freedberg, D. I.; Hall, B. G. J. Bacteriol. 1999, 181, 7339-7345. (f) He, X. M.; Liu, H.-W. Annu. Rev. Biochem. 2002, 71, 511-535. (g) Thompson, J.; Hess, S.; Pikis, A. J. Biol. Chem. 2004, 279, 1553-1561. (h) Yip, V. L. Y.; Varrot, A.; Davies, G. J.; Rajan, S. S.; Yang, X.; Thompson, J.; Anderson, W. F.; Withers, S. G. J. Am. Chem. Soc. 2004, 126, 8354-8355.
23. Hunter, T. Phil. Trans. R. Soc. B 2012, 367, 2513–2516.
24. R. Robison, E. J. King, Biochem. J. 1931, 25, 323–328.
25. Kornfeld, S.; Mellman, I. Annu. Rev. Cell Biol. 1989, 5, 483-525.
26. S. Kornfeld. Annu. Rev. Biochem. 1992, 61, 307-330.
27. De Duve, C.; Pressman, B. C.; Gianetto, R.; Wattiaux, R.; Appelmans, F. Biochem. J. 1955, 60, 604-617.
28. Maria, F. C.; Maria, J. P.; Alves, S. Molecular Genetics and Metabolism. 2012, 105, 542-550.
29. a) Pollak, A.; Baughn, R. L.; Whitesides, G. M. J. Am. Chem. Soc. 1977, 99, 2366-2367. b) Wong, C. H.; Whitesides, G. M. J . Am. Chem. Soc. 1981, 16, 4890-4899. c) Chenault, H. K.; Mandes, R. F.; Hornberger, K. R. J. Org. Chem. 1997, 62, 331-336.
30. Hansen, C. A.; Dean, A. B.; Draths, K. M.; Frost, W. J. Am. Chem. Soc. 1999, 121, 3799-3800.
31. a) Herk, T. V.; Hartog, A. F.; Van der Burg, A. M.; Wever, R. Adv. Synth. Catal. 2005, 347, 1155-1162. b) Babich, L.; Hartog, A. F.; Van der Horst, M.A. and Wever, R. Chem. Eur. J. 2012, 18, 6604-6609.
32. Neuberg, C.; Lustig, H.; Rathenberg, M. A. Arch. Biochem. 1943, 3, 33-44.
33. Colowick, B. P.; Sutherland, E. W. J. Biol. Chem. 1942, 44, 423-437.
34. Rodriguez-Perez, T.; Lavandera, I.; Fernandez, S.; Sanghvi, Y. S.; Ferrero, M.; Gotor, V. Eur. J. Org. Chem. 2007, 2769-2778.
35. Uchiyama, M.; Asoy, Y.; Noyori, R.; Hayakawa, Y. J. Org. Chem. 1993, 58, 373-379.
36. Marugg, J. E.; McLaughlin, L. W.; Piel, N.; Tromp, M.; van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 1983, 24, 3989-3992.
37. Burger, A.; Anderson, J. J. J. Am. Chem. Soc. 1957, 79, 3575-3579.
38. Perich, J. W.; Johns, R. B. Tetrahedron Lett. 1987, 28, 101-102.
39. Matta, K. L.; Chowdhary, M. S.; Jain, R. K. Carbohydr. Res. 1986, 150, 167-175.
40. a) Jones, S.; Selitsianos, D. Org. Lett. 2002, 4, 3671-3673. b) Jones, S.; Smanmoo, C. Org. Lett. 2005, 7, 3271-3274.
41. (a) Drueckhamer, D. G.; Hennen, J. W.; Pederson, R. L.; Barbas, C. F.; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis. 1991, 7, 499-525. (b) Khan, R.; Groppen, L.; Konpwicz, P. A.; Matulová, M.; Paoletti, S. Tetrahedron Lett. 1993, 34, 7767-7770. (c) Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395-8401. (d) Kim, M.-J.; Choi, M. Y.; Lee, J. K.; Ahn, Y. J. Mol. Catal. B, 2003, 26, 115-126. (e) Chien, T.-C.; Chern, J.-W.; Carbohydr. Res. 2004, 339, 1215-1217. (f) Ganske, F.; Bornscheuer, U. T. Org. Lett. 2005, 7, 3097-3098.
42. Liu, C.-Y.; Pawar, V. D.; Kao, J.-Q.; Chen, C.-T. Adv. Synth. Catal. 2010, 352, 188-194.
43. (a) Parang, K.; Fournier, E. J.-L.; Hindsgaul, O. Org. Lett. 2001, 3, 307-309. (b) Ahmadibeni, Y.; Parang, K. J. Org. Chem. 2005, 70, 1100-1103.
44. T. Ronnow, M.; Meldal, M.; Bock, K. Carbohydr. Res. 1992, 235, 115-127.
45. a) Lepenies, B.; Seeberger, P. H. Immunopharmacol. Immunotoxicol. 2010, 32, 196–207; b) Wu, C.-Y.; Wong, C.-H. Chem. Commun. 2011, 47, 6201-3207; c) Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046-1051.
46. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, Hoboken NJ, 2007.
47. Filice, M.; Guisan, J. M.; Palomo, J. M. Curr. Org. Chem. 2010, 14, 516-532.
48. Lalonde, M.; Chan, T. H. Synthesis 1985, 817.
49. Olsson, L.-I. Acta Pharm. Suec. 1986, 23, 370.
50. Kuwajima, I.; Nakamura, E. Acc. Chem. Res. 1985, 18, 181-187.
51. Colvin, E. W. “Silicon in Organic Synthesis”, Butterworths, 1981.
52. Tanabe, Y.; Murakami, M.; Kitaichi, K.; Yoshida, Y. Tetrahedron Lett. 1994, 35, 8409-8412.
53. Lukevics, E. Russ. Chem. Rev. 1974, 43, 140.
54. Voaden, D. J.; Waters, R. M. Org. Prep. Proced. Int. 1976, 8, 227.
55. Kierzek, R. Nucleosides & Nucleotides 1985, 4, 641.
56. a) Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896-899. b) Wang, C.-C.; Kulkarni, S.-S.; Lee, J.-C.; Luo, S.-Y.; Hung, S.-C. Nat. Protoc. 2008, 3, 97-113. c) Chang, K.-L.; Zulueta, M. M. L.; Liu, X.-A.; Zhong, Y.-Q.; Hung, S.-C. J. Org. Chem. 2010, 75, 7424-7427. d) Huang, T.-Y.; Zulueta, M. M. L.; Hung, S.-C. Org. Lett. 2011, 13, 1506-1509. e) Wang, C.-C.; Zulueta, M. M. L.; Hung, S.-C. Chimia 2011, 65, 54-58. d) Hu, Y.-P.; Lin, S.-Y.; Huang, C.-Y.; Zulueta, M. M.; Liu, J.-Y.; Chang, W.; Hung, S.-C. Nat. Chem. 2011, 3, 557-563.
57. Francais, A.; Urban, D.; Beau, J.-M. Angew. Chem. 2007, 119, 8816–8819. b) Bourdreux, Y.; Lemétais, A.; Urban, D.; Beau, J.-M. Chem. Commun. 2011, 47, 2146-2148. c) Despras, G.; Urban, D.; Vauzeilles, B.; Beau, J.-M. Chem. Commun. 2014, 50, 1067-1069.
58. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
59. a) Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1979, 20, 4679-4680. b) Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.; Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367-4370. c) Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Lu, L.-D.; Hung, S.-C. Angew. Chem. 2002, 114, 2466-2468. d) Yang, W.-C.; Lu, X.-A.; Kulkarni, S. S.; Hung, S.-C. Tetrahedron Lett. 2003, 44, 7837-7840.
60. a) Uchiyama, T.; Hindsgaul, O. Synlett 1996, 499-501; b) Uchiyama, T.; Hindsgaul, O. J. Carbohydr. Chem. 1998, 17, 1181–1190.
61. a) Bhat, A.; Gervay-Hague, J. Org. Lett. 2001, 3, 2081-2084; b) Du, W.; Gervay-Hague, J. Org. Lett. 2005, 7, 2063-2065; b) Du, W.; Kulkarni, S. S.; Gervay-Hague, J. Chem. Commun. 2007, 2336-2338; c) Kulkarni, S. S.; Gervay-Hague, J. Org. Lett. 2008, 10, 4739-4742; d) Schombs, M.; Park, F. E.; Du, W.; Kulkarni, S. S.; Gervay-Hague, J. J. Org. Chem. 2010, 75, 4891-4898.
62. Witschi, M. A.; Gervay-Hague, J. Org. Lett. 2010, 12, 4312-4315.
63. Hsieh, H-W.; Schombs, M. W.; Witschi, M. A.; Gervay-Hague, J. J. Org. Chem. 2013, 78, 9677-9688.
64. Hsieh, H-W.; Schombs, M. W.; Witschi, M. A.; Gervay-Hague, J, J. Org. Chem. 2014, 79, 1736-1748.
65. Davis, R. A.; Fettinger, J. C.; Gervay-Hague, J. J. Org. Chem. 2014, 79, 8447-8452.
66. Nguyen, H. Q.; Davis, R. A.; Gervay-Hague, J, Angew. Chem. Int. Ed. 2014, 53, 13400-13403.
67. Park, S. S. and Gervay-Hague, J. Org. Lett. 2014, 16, 5044-5047.
68. Adduci, L. L.; McLaughlin, M. P.; Bender, T. A.; Becker, J. J.; Gagne, M. R. Angew. Chem. Int. Ed. 2014, 53, 1646 -1649.
69. Cui, Y.; Cheng, Z.; Mao, J.; Yu, Y. Tetrahedron Lett. 2013, 54, 3831-3833.
70. a) Oubiana, R.T.; Das, B. C.; Defaye, J.; Mompon, B.; Toubiana, M.-J. Carbohydr. Res. 1975, 44, 308-312; b) Gensler, W. J.; Alam, I. J. Org. Chem. 1977, 42, 130-135; c) Gensler, W. J.; Chhatwal, V. K.; Alam, I.; Constantino, E.; Tarnowski, G. S.; Pimm, M. V.; Baldwin, R. W. Cancer Immunol. Immunother. 1980, 9, 101-109; d) Datta, A. K.; Takayama, K.; Nashed, M. A.; Anderson, L. Carbohydr. Res. 1991, 218, 95-109; e) Johnson, D. A. Carbohydr. Res. 1992, 237, 313-318; f) Rønnow, T. E. C. L.; Meldal, M.; Bock, K. Carbohydr. Res. 1994, 260, 323-328; g) Johnson, D. A.; Livesay, M. T. J. Carbohydr. Chem. 1998, 17, 969-974; h) Al Dulayymi, J. R.; Baird, M. S.; Maza-Iglesias, M.; Beken, S. V.; Grooten, J. Tetrahedron Lett. 2009, 50, 3702-3705.
71. Lemétais, A.; Bourdreux, Y.; Lesot, P.; Farjon, J.; Beau, J.-M. J. Org.Chem. 2013, 78, 7648-7657.
72. Sarpe, V. A.; Kulkarni, S. S. Org. Lett. 2014, 16, 5732-5735.
73. (a) Sarpe, V. A.; Kulkarni, S. S. J. Org. Chem. 2011, 76, 6866−6870. (b) Sarpe, V. A.; Kulkarni, S. S. Org. Biomol. Chem. 2013, 11, 6460-6465.
74. Liu, C.; Mariano, P. S. Tetrahedron Lett. 2015, Accepted (http://dx.doi.org/10.1016/j.tetlet.2014.10.003)
75. Joseph, A. A.; Chang, C.-W.; Wang, C.-C. Chem. Commun. 2013, 49, 11497-11499.
76. Haines, A. H.; Massy, D. J. R. Synthesis 1996, 12, 1422-1424.
77. a) Sweeley, C. C.; Bentley, R.; Makita M. and Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2507; (b) Karkkainen, J. and Vihko, R. Carbohydr. Res. 1969, 10, 113-120.
78. a) Bhat, A. S.; Gervay-Hague, J. Org. Lett. 2001, 13, 2081-2084. b) Johnson, Carbohydr. Res. 1992, 237, 313-318. c) Odinokov; Savchenko; Nazmeeva; Galyautdinov; Khalilov. Russian Chemical Bulletin. 2002, 51, 1937 - 1939; d) Andrews, M. A. Carbohydr. Res. 1989, 194, 1-20. e) Olah, G. A.; Klumpp, D. A. Synthesis 1997, 7, 744 -746.
79. Bruynes, C. A. and Jurriens, T. K. J. Org. Chem. 1982, 47, 3966-3969.
80. Zareyeea, D. and Karimi, B. Tetrahedron Lett. 2007, 48, 1277-1278.
81. Khazaei, A.; Zolfigol, M. A.; Rostami, A.; A. Choghamarani, G. Catal. Commun. 2007, 8, 543-547.
82. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Chahardahcheric, S. and Tavakoli, Z. J. Organomet. Chem. 2008, 693, 2041-2046.
83. Zang, Z. H.; Li, T. S.; Yang, F.; Fu, C. G. Synth. Commun. 1998, 28, 3105.
84. Tillu,V. H.; Jadhav, V.H.; Borate H. B.; Wakharkar, R. D. Arkivoc. 2004, 83-88.
85. Shaterian, H. R.; Shahrekipoor F.; Ghashang, M. J. Mol. Catal. A: Chem. 2007, 272-275.
86. Khazaei, K.; Zolfigol, M.A.; Tanbakouchian, Z.; Shiri, M.; Niknam, K.; Saien, J. Catal. Commun. 2007, 8, 917-920.
87. Karimi, B.; Golshani, B. J. Org. Chem. 2000, 65, 7228-7230.
88. Mojtahedi, M. M.; Abbasi, H.; Abaee, M. S. J. Mol. Catal. A: Chem. 2006, 250, 6-10.
89. Shaterian, H. R.; Doostmohammadi R. and Ghashang, M. Chin. J. Chem. 2008, 26, 1709-1714.
90. Firouzabadi, H.; Iranpoor, N.; Jafari A. A. and Jafari, M. R. J. Organomet. Chem. 2008, 693, 2711-2714.
91. Azizi, N.; Saidi, M. R. Organometallics 2004, 23, 1457-1458.
92. Cossy, J.; Pale, P. Tetrahedron Lett. 1987, 28, 6039-6042.
93. Bandgar, B.P.; Wadgaonkar P.P. Synth. Commun. 1997, 27, 2069-2074.
94. Curini, M.; Epifano, F.; Marcotullio, M.C.; Rosati, O.; Costantino, U. Synth. Commun. 1999, 29, 541-546.
95. Rajagopal, G.; Lee, H.; Kim, S. S. Tetrahedron. 2009, 65, 4735-4741.
96. Firouzabadi, H.; Iranpoor, N. Farahi, S. Catal. Commun. 2009, 10, 1547-1550.
97. Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Gassamipour, S. J. Organomet. Chem. 2004, 689, 3197-3202.
98. a) Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Gassamipour, S.; Amoozgar, Z. Tetrahedron Lett. 2003, 44, 891-896. b) Akhlaghinia, B.; Tavakoli, S. Synthesis 2005, 1775-1886.
99. Kadam, S.T.; Kim, S. S. J. Organomet. Chem. 2009, 694, 2562-2566.
100. Zolfigol, M. A.; Khazaei, A.; Kolvari, E.; Koukabia, N.; Soltania, H.; Behjuniaa, M. Helv. Chim. Acta. 2010, 93, 1894-1911.
101. Narsaiah, A. V. J. Organomet. Chem. 2007, 692, 3614-3618.
102. Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Gassamipour, S. Synthesis 2005, 595-599.
103. Firouzabadi, H.; Karimi, B. Synth. Commun. 1993, 23, 1633-1641.
104. Firouzabadi, H.; Iranpoor, N.; Amani, K.; Nowrouzi, F. J. Chem. Soc., Perkin Trans. 1, 2002, 2601-2604.
105. Shaterian, H. R.; Fahimi, N.; Azizi, K. Res Chem Intermed. 2011, DOI 10.1007/s11164-013-1247-4.
106. Khazaei, A.; Zolfigol, M. A.; Tanbakouchian, Z.; Shiri, M.; Niknam, K.; Saien, J. Catal. Commun. 2007, 8, 917-920.
107. Khazaei, A.; Rostamib, A.; Mahboubifara, M. J. Chin. Chem. Soc. 2007, 54, 483-487.
108. Zareyee, D.; Asghari, R.; Khalilzadeh, M. A. Chin. J. Catal. 2011, 32, 1864-1868.
109. Vrushali, H.; Jadhav, K.; Kumar, S. A.; Chaudhari, V.D. and Dhavale, D. D. Synth. Commun. 2007, 37, 1363-1370.
110. Yadegaria, M.; Moghadamb, M.; Tangestaninejadb, S.; Mirkhanib, V.; Mohammadp, I. Polyhedron. 2012, 31, 332-338.
111. Ghorbani, V. R.; Zolfigol, M. A.; Chegeny, M.; Veisi, H. Tetrahedron Lett. 2006, 47, 4505-4508.
112. Shuirakawa, E.; Hironaka, K.; Otsuka, H.; Hayashi, T. Chem. Commun. 2006, 3927-3929.
113. Reis, P. M.; Royo, B. Catal. Commun. 2007, 8, 1057-1059.
114. Ghorbani-C. A.; Zolfigol, M. A.; Hajjami, M.; Jafari, S. J. Chin. Chem. Soc. 2008, 55, 1208-1213.
115. Niknam, K.; Zolfigol, M A.; Chehardoli, G.; Dehghanian, M. Chin. J. Catal. 2008, 29, 901-906.
116. Mojtahedi, M.M.; Abaee, M.S.; Eghtedari, M. Appl. Organometal. Chem. 2008, 22, 529-532.
117. Shirini, F.; Ghaffari Khaligh, N. J. Iran. Chem. Soc. 2012, 9, 495-502.
118. Firouzabadi, H.; Sardarian, A.R.; Khayat, Z. Iran. J. Chem. Chem. Eng. 1996, 15, 91.
119. Firouzabadi, H.; Iranpoor, N.; Eslami, Sh. Tetrahedron Lett. 1999, 40, 4055-4058.
120. Iranpoor, N.; Shekarriz, M. Bull. Chem. Soc. Jpn. 1999, 72, 455-458.
121. Ren, Y.; Li, M.; Yang, J.; Peng, J.; Gua, Y. Adv. Synth. Catal. 2011, 353, 3473 -3484.
122. Akhlaghinia, B.; Tavakoli, S. Synthesis 2005, 1775-1777.
123. Shaterian, H. R.; Fahimi, N.; Azizi, K. Phosphorus, Sulfur, and Silicon 2011, 186, 1604–1611.
124. Wu, L.; Sun, P.; Yan, F. Phosphorus, Sulfur, and Silicon 2011, 186, 2055-2060.
125. Park J.-W.; Jun, C.-H. Org. Lett. 2007, 9, 4073-4076.
126. Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 6734-6737.
127. Aghapour, G.; Moghaddam, A. K. and Nadali, S. J. Chin. Chem. Soc. 2015. DOI: 10.1002/jccs.201300624.
128. Kadam, S. T.; Kim, S. S. Green Chem. 2010, 12, 94-98.
129. Joseph, A. A.; Dhurandhare, V. M.; Chang, C.-W.; Verma,V. P.; V.; Mishra, P. G.; Ku, C.-C.; Lin, C.-C.; Wang, C.-C. Chem. Commun. 2015, 51, 104-106.
130. Emde, H.; Domsch, D.; Feger, H.; Frick, U.; Götz, A.; Hergott, H. H.; Hoffman, K.; Kober, W.; Krägeloh, K.; Oesterle, T.; Steppan, W.; West, W.; Simchen, G. Synthesis 1982, 1-26.
131. Joseph, A. A.; Verma, V. P.; Liu, X.-Y.; Wu, C.-H.; Dhurandhare, V. M.; Wang, C.-C. Eur. J. Org. Chem. 2012, 744-753.
132. Bukowska, M.; Maciejewski, M.; Prejzner, J. Carbohydr. Res. 1998, 308, 275-279.
133. a) Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. Chem. Commun. 1996, 2625-2626. b) Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342-2347.
134. Denino, M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669-672.
135. Jiang, L.; Chan, T. H. Tetrahedron Lett. 1998, 39, 355-358.
136. Lu, X.-A.; Chou, C.-H.; Wang, C.-C.; Hung, S.-C. Synlett. 2003, 1364-1366.
137. Same one-pot procedures immediately after traditional TMSCl and triethylamine (Et3N) silylation were tested, but the reaction could not proceed any further.
138. Patel, M. K.; Davis, B. G. Org. Lett. 2013, 15, 346-349.
139. (a) Eguchi, T.; Sasaki, S.; Huang, Z.; Kakinuma, K. J. Org. Chem. 2002, 67, 3979-3984. (b) Yamauchi, N.; Kakinuma, K. J. Org. Chem. 1995, 60, 5614-5619. (c) Aminocyclitol antibiotics (Ed.: Jr Rinehart, K. L.; Suami, T.), ACS Symposium Series No.125; American Chemical Society, Washington, DC, 1980. (d) Jr Rinehart, K. L.; Stroshane, R. M. J. Antibiotic. 1976, 29, 319-353.
140. Champmartin, D.; Rubini, P.; Lakatos, A.; Kiss, T. J. Inorg. Biochem. 2001, 84, 13-21.
141. Foufelle, F.; Gouhot, B.; Pegorier, J. P.; Perdereau, D.; Girard, J.; Ferre, P. J. Biol. Chem. 1992, 267, 20543-20546.
142. Cabib, E.; Leloir, L. F. J. Biol. Chem. 1958, 231, 259-275.
143. (a) Backus, K. M.; Boshoff, H. I.; Barry, C. S.; Bouturwira, O.; Patel, M. K.; D’Hooge, F.; Lee, S. S.; Via, L. E.; Tahlan, K.; Barry III, C. E.; Davis, B. G. Nat. Chem. Biol. 2011, 7, 228-235. (b) Fernandez, O.; Bethencourt, L.; Quero, A.; Sangwan, R. S.; Clement, C. Trends in Plant. Sci. 2010, 15, 409-417. (c) Paul, M. J.; Primavesi, D.; Jhurreea, D.; Zhang, Y. Annu. Rev. Plant Biol. 2008, 59, 417-441.
144. Rolland, F.; Baena-Gonzalez, E.; Sheen, J. Annu. Rev. Plant Biol. 2006, 57, 675-709.
145. Goddijn, O. J.; Van Dun, K. Trends Plant Sci. 1999, 4, 315-319.
146. Eleutherio, E. C. A.; Araujo, P. S.; Panek, A. D. Cryobiology. 1993, 30, 591-596.
147. Paul, M. Curr. Opin. Plant. Biol. 2007, 10, 303-309.
148. Higashiyama, T. Pure Appl. Chem. 2002, 74, 1263-1269.
149. Eastmond, P. J.; Graham, I. A. Curr. Opin. Plant. Biol. 2003, 6, 231-235.
150. (a) Avonce, N.; Mendoza-Vargas, A.; Morett, E.; Iturriaga, G. Bmc Evolutionary Biol. 2006, 6. (b) Streeter, J. G.; Bhagwat, A. Can. J. Microbiol. 1999, 45, 716-721. (c) Wannet, W. J. B.; Den Camp, H.; Wisselink, H. W.; Van der Drift, C.; Van Griensven, L.; Vogels, G. D. Biochimica Et Biophysica Acta-General Subjects 1998, 1425, 177-188. (d) Schiraldi, C.; Di Lernia, I.; De Rosa, M. Trends in Biotechnology. 2002, 20, 420-425. (e) Ying, L.; Gervay-Hague, J. Carbohydr. Res. 2004, 339, 367-375. (f) Ryu, S. I.; Park, C. S.; Cha, J.; Woo, E. J.; Lee, S. B. Biochem.Biophys. Res. Commun. 2005, 329, 429-436. (g) Cabib, E.; Leloir, L. F. 1958, 231, 259-275.
151. Leloir, L. F.; Cabib, E. J. Am. Chem. Soc. 1953, 75, 5445-5446.
152. Elbein, A. D.; Pan, Y. T.; Pastuszak, I.; Carroll, D. Glycobiology 2003, 13, 17R-27R.
153. Wilson, R. A.; Jenkinson, J. M.; Gibson, R. P.; Littlechild, J. A.; Wang, Z. Y.; Talbot, N. J. Embo Journal. 2007, 26, 3673-3685.
154. Schluepmann, H.; Pellny, T.; van Dijken, A.; Smeekens, S.; Paul, M. Proc. Natl. Acad. Sci. USA. 2003, 100, 6849-6854.
155. Pellny, T. K.; Ghannoum, O.; Conroy, J. P.; Schluepmann, H.; Smeekens, S.; Andralojc, J.; Krause, K. P.; Goddijn, O.; Paul, M. J. Plant Biotechnol J, 2004, 2, 71-82.
156. Kolbe, A.; Tiessen, A.; Schluepmann, H.; Paul, M.; Ulrich, S.; Geigenberger, P. Proc. Natl. Acad. Sci. USA. 2005, 102, 11118-11123.
157. Ekkehard Neuhaus, H.; Stitt, M. Planta 1990, 182, 445-454.
158. Geigenberger, P.; Stitt, M.; Fernie, A. R. Plant, Cell & Environment 2004, 27, 655-673.
159. Ballicora, M. A.; Frueauf, J. B.; Fu, Y. B.; Schurmann, P.; Preiss, J. J. Biol. Chem. 2000, 275, 1315-1320.
160. Lunn, J. E.; Feil, R.; Hendriks, J. H. M.; Gibon, Y.; Morcuende, R.; Osuna, D.; Scheible, W. R.; Carillo, P.; Hajirezaei, M. R.; Stitt, M. Biochem. J. 2006, 397, 139-148.
161. Lunn, J. E.; MacRae, E. Curr. Opin. Plant Biol. 2003, 6, 208-214.
162. Monsan, P.; Remaud-Simeon M.; Andre, I. Curr. Opin. Microbiol. 2010, 13, 293-300.
163. Selvendran, R. R.; Isherwood, F. A. Phytochemistry 1970, 9, 553-536.
164. Krause, K. P.; Stitt, M. Phytochemistry 1992, 31, 1143-1146.
165. Breg, J.; Romijin, D.; Halbeek, H. V.; Vliegenthart, J. F. G.; Visser, R. A.; Haasnoot, C. A. G. Carbohydr. Res. 1988, 174, 23-36.
166. Yip, V. L. Y.; Withers, S. G. Angew. Chem. Int. Ed. 2006, 45, 6176-6179.
167. Tarelli, E.; Wheeler, S. F. Carbohydr. Res. 1994, 261, 25-36.
168. MacDonald, D. L.; Wong, Y. K, Biochim. Biophys. Acta 1964, 86, 390-392.
169. Perez-Victoria, I.; Kemper, S.; Patel, M. K.; Edwards, J. M.; Errey, J. C.; Primavesi, L. F.; Paul, M. J.; Claridge, T. D. W.; Davis, B. G. Chem. Commun. 2009, 45, 5862-5864.
170. Patel, M. K.; Davis, B. G. Org. Biomol. Chem. 2010, 8, 4232-4235.
171. T. Ronnow, M.; Meldal, M.; Bock, K. Carbohydr. Res. 1994, 260, 323-328.
172. Nilsson, J.; Kraszewski, A.; Stawinski, J. J. Chem. Soc., Perkin Trans. 2. 2001, 2263-2266.

Chapter-2
1. Anderson, R. J.; Newman, M. S. J. Biol. Chem. 1933, 101, 499-504.
2. Asselineau, C.; Asselineau, J. Prog. Chem. Fats other Lipids 1978, 16, 59-99.
3. Bloch, H. J. Exp. Med. 1950, 91, 197-218.
4. Brennan P. J.; Nikaido, H. Annu. Rev. Biochem. 1995, 64, 29-63.
5. (a) Converse, S. E.; Mougous, J. D.; Leavell, M. D.; Leary, J. A.; Bertozzi C. R.; Cox, J. S. Proc. Natl. Acad. Sci. USA. 2003, 100, 6121-6126. (b) Rousseau, C.; Neyrolles, O.; Bordat, Y.; Giroux, S.; Sirakova, T. D.; Prevost, M.-C.; Kolattukudy, P. E.; Gicquel, B.; Jackson, M. Cell Microbiol. 2003, 5, 405-415. (c) Rousseau, C.; Turner, O.; Rush, C. E.; Bordat, Y. T.; Sirakova, D.; Kolattukudy, P. E.; Ritter, S. I.; Orme, M.; Gicquel, B.; Jackson, M. Infect. Immun. 2003, 71, 4684-4690. (d) Chesne-Seck, M.-L.; Barilone, N.; Boudou, F.; Asensio, J. G.; Kolattukudy, P. E.; Martin, C.; Cole, S. T.; Gicquel, B.; Gopaul, D. N.; Jackson, M. J. Bacteriol. 2008, 190, 1329-1334. (e) Passemar, C.; Arbues, A.; Malaga, W.; Mercier, I.; Moreau, F.; Lepourry, L.; Neyrolles, O.; Guilhot, C.; Astarie-Dequeker, C. Cell Microbiol. 2014, 16, 195-213.
6. (a) Kumar, P.; Schelle, M. W.; Jain, M.; Lin, F. L.; Petzold, C. J.; Leavell, M. D.; Leary, J. A.; Cox, J. S.; Bertozzi, C. R. Proc. Natl. Acad. Sci. USA. 2007, 104, 11221-11226. (b) Gilmore, S. A.; Schelle, M. W.; Holsclaw, C. M.; Leigh, C. D.; Jain, M.; Cox, J. S.; Leary, J. A.; Bertozzi, C. R. ACS Chem. Biol. 2012, 7, 863-870.
7. Bricard, G.; Porcelli, S. A. Cell Mol. Life Sci. 2007, 64, 1824-1840.
8. Wu, C.-H.; Wang, C.-C.; Org. Biomol. Chem. 2014, 12, 5558-5562.
9. (a) Pavia, A. A.; Rocheville, J.-M.; Ung, S. N. Carbohydr. Res. 1980, 79, 79-89. (b) Nishizawa, M.; Garcia, D. M.; Noguchi, Y.; Komatsu, K.; Hatakeyama, S.; Yamada, H. Chem. Pharm. Bull. 1994, 42, 2400-2402. (c) Posner, G. H.; Bull, D. S. Tetrahedron Lett. 1996, 37, 6279-6282. (d) Cipolla, L.; Lay, L.; Nicatra, F.; Panza, L.; Russo, G. Tetrahedron Lett. 1994, 35, 8669-8670. (e) Yoshimura, J.; Hara, K.; Sato, T.; Hashimoto, H. Chem. Lett. 1983, 12, 319-320. (f) Ronnow, T.; Meldal, M.; Bock, K. Tetrahedron: Asymmetry 1994, 5, 2109-2122.
10. (a) Pratt, M. R.; Leigh, C. D.; Bertozzi, C. R. Org. Lett. 2003, 5, 3185-3188. (b) Leigh, C. D.; Bertozzi, C. R. J. Org. Chem. 2008, 73, 1008-1017.
11. Bassily, R. W.; El-Sokkary, R.I.; Silwanis, B. A.; Nematalla, A. S.; Nashed, M. A. Carbohydr. Res. 1993, 239, 197-207.
12. Khan, A. A.; Chee, S. H.; McLaughlin, R. J.; Harper, J. L.; Kamena, F.; Timmer, M. S. M.; Stocker, B. L. ChemBioChem 2011, 12, 2572-2576.
13. Kanemaru, M.; Yamamoto, K.; Kadokawa, J. Carbohydr. Res. 2012, 357, 32-40.
14. Paul, K. J.; Twibanire, K.; Grindley, T. B. J. Org. Chem. 2013, 78, 363-369.
15. Guiard, J.; Collman, A.; Gilleron, M.; Mori, L.; De Libero, G.; Prandi, J.; Puzo, G. Angew. Chem. Int. Ed. 2008, 47, 9734-9738.
16. Abik, A.; Goren, M. B. Carbohydr. Res. 1984, 127, 211-216.
17. Geerdink, D.; Ter Horst, B.; Lepore, M.; Mori, L.; Puzo, G.; Hirsch, A. K. H.; Gilleron, M.; De Livero, G.; Minnaard, A. J. Chem. Sci. 2013, 4, 709-716.
18. Geerdink, D.; Minnaard, A. J. Chem. Comm. 2014, 50, 2286-2288.
19. Francais, A.; Urban, D.; Beau, J.-M. Angew. Chem. 2007, 119, 8816–8819. b) Bourdreux, Y.; Lemétais, A.; Urban, D.; Beau, J.-M. Chem. Commun. 2011, 47, 2146-2148. c) Despras, G.; Urban, D.; Vauzeilles, B.; Beau, J.-M. Chem. Commun. 2014, 50, 1067-1069.
20. (a) Sarpe, V. A.; Kulkarni, S. S. J. Org. Chem. 2011, 76, 6866−6870. (b) Sarpe, V. A.; Kulkarni, S. S. Org. Biomol. Chem. 2013, 11, 6460-6465.
21. Gensler, W. J.; Alam, I. J. Org. Chem. 1977, 42, 130-135.
22. Sarpe, V. A.; Kulkarni, S. S. Org. Lett. 2014, 16, 5732-5735.
23. Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, Hoboken NJ, 2007.
24. Barry, C. S.; Backus, K. M.; Barry III, C. E.; Davis, B. G. J. Am. Chem. Soc. 2011, 133, 13232-13235.
25. Joseph, A. A.; Chang, C.-W.; Wang, C.-C. Chem. Commun. 2013, 49, 11497-11499.
26. Joseph, A. A.; Verma, V. P.; Liu, X.-Y.; Wu, C.-H.; Dhurandhare, V. M.; Wang, C.-C. Eur. J. Org. Chem. 2012, 744-753.
27. Kohei, Y.; Hikaru, F.; Munetaka, K. Org. Lett. 2012, 14, 5026-5029.
28. Backus, K. M.; Boshoff, H. I.; Barry, C. S.; Bouturwira, O.; Patel, M. K.; D’Hooge, F.; Lee, S. S.; Via, L. E.; Tahlan, K.; Barry III, C. E.; Davis, B. G. Nat. Chem. Biol. 2011, 7, 228-235.


Chapter-3

1. Varki, A.; Cummings, D. R.; Esko, J. D.; Freeze, H. H.; Stanley, P.; Bertozzi, C. R.; Hart, G. W.; Etzler, M. E. Essentials of Glycobiology, 2nd edition. Cold Spring Harbor, New York. 2008.
2. (a) Bryant, C. E.; Spring, D. R.; Gangloff, M.; Gay, N. J. Nat. Rev. Microbiol. 2010, 8, 8-14. (b) Paulick, M. G.; Bertozzi, C. R. Biochemistry 2008, 47, 6991-7000. (c) Gandhi, N. S.; Mancera, R. L. Chem. Biol. Drug Des. 2008, 72, 455-482. (d) Wang, L.-X.; Huang, W. Curr. Opin. Chem. Biol. 2009, 13, 592-600. (e) Taube, S.; Jiang, M.; Wobus, C. E. Viruses 2010, 2, 1011-1049. (f) Salton, M. R. J. Annu. Rev. Biochem. 1965, 34, 143-174. (g) Emmadi, M.; Kulkarni, S. S. Nat. Protoc. 2013, 8, 1870-1889.
3. (a) Boons, G-J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539-4565. (b) Comb, D. G.; Roseman, S. J. Biol. Chem. 1960, 235, 2529-2537. (c) Roseman, S. Federation Proc. 1962, 21, 1075.
4. Blix, G. Z. Physiol. Chem. 1936, 240, 43-49.
5. Waksman, S. A.; Katz, E.; Lechevalier, H. J Lab Clin Med. 1950, 36, 93-99.
6. Gutierrez-Moreno, N. J.; Medrano, F.; Yatsimirsky, A. K. Org. Biomol. Chem. 2012, 10, 6960-6972.
7. Liang, C.; Pedersen, J. A.; Balser, T. C. J. Chromatogr. A. 2009, 1216, 5296-5301.
8. Umezawa, H.; Hooper, I. R. Aminoglycoside Antibiotics, ed. Springer, New York, Heidelberg, 1982.
9. Fuster, M. M.; Esko, J. D. Nat. Rev. Cancer 2005, 5, 526-542.
10. Berg, Tymoczko, Stryer. Biochemistry, 7th ed. W. H. Freeman and Company. London. 2012.
11. Enugala, R.; Carvalho, L. C. R.; Pires, M. J. D.; Marques, M. M. B. Chem. Asian J. 2012, 7, 2482-2501.
12. Schotton, C. Beriche der deutschen chemischen Gesellschaft 1884, 17, 2544-2547.
13. Baumann, E. Beriche der deutschen chemischen Gesellschaft 1886, 19, 3218-3222.
14. (a) Simpkins, N. S.; Stokes, S. Tetrahedron Lett. 1992, 33, 793-796. (b) Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032. (c) Jia, Y.; Ma, N.; Liu, Z. M.; Bois-Choussy, E.; Gonzalez-Zamora, A.; Malabarba, C.; Brunati.; Zhu, J. Chem. Eur. J. 2006, 12, 5334-5351. (d) Jung, M. E.; Dong, T. A.; Cai, X. Tetrahedron Lett. 2011, 52, 2533-2536.
15. Silva, D. J.; Wang, H.; Allanson, N. M.; Jane, R. K.; Sofia, M. J. J. Org. Chem. 1999, 64, 5926-5929.
16. (a) Krishnamurthy, V. R.; Dougherty, A.; Kamat, M.; Song, X.; Cummings, R. D.; Chaikof, E. L. Carbohydr. Res. 2010, 345, 1541-1547. (b) Roychoudhury, R.; Pohl, N. L. B. Org. Lett. 2014, 16, 1156-1159.
17. (a) Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896-899. (b) Wang, C.-C.; Kulkarni, S.-S.; Lee, J.-C.; Luo, S.-Y.; Hung, S.-C. Nat. Protoc. 2008, 3, 97-113.
18. (a) Joseph, A. A.; Verma, V. P.; Liu, X.-Y.; Wu, C.-H.; Dhurandhare, V. M.; Wang, C.-C. Eur. J. Org. Chem. 2012, 744-753. (b) Joseph, A. A.; Chang, C.-W.; Wang, C.-C. Chem. Commun. 2013, 49, 11497-11499.
19. Chang, K.-L.; Zulueta, M. M. L.; Lu, X.-A.; Zhong, Y.-Q.; Hung, S.-C. J. Org. Chem. 2010, 75, 7424-7427.
20. Despras, G.; Urban, D.; Vauzeilles, B.; Beau, J.-M. Chem. Commun. 2014, 50, 1067-1069.
21. Ko, Y.-C.; Tsai, C.-F.; Wang, C.-C.; Dhurandhare, V. M.; Hu, P.-L.; Su, T.-Y.; Lico, L. S.; Zulueta, M. M. L.; Hung, S.-C. J. Am. Chem. Soc. 2014, 136, 14425-14431.
22. (a) Minuth, T.; Irmak, M.; Groschner, A.; Lehnert, T.; Boysen, M. M. K. Eur. J. Org. Chem. 2009, 997-1008. (b) Irmak, M.; Lehnert, T.; Boysen, M. M. K. Tetrahedron Lett. 2007, 48, 7890-7893. (c) Irmak, M.; Groschner, A.; Boysen, M. M. K. Chem. Commun. 2007, 177-179. (d) Irmak, M.; Boysen, M. M. K. Adv. Synth. Catal. 2008, 350, 403-410. (e) Minuth, T.; Boysen, M. M. K. Synthesis 2010, 16, 2799-2803.
23. Yin, A. L.; Dalsin, M. C.; Sizovs, A.; Reineke, T. M.; Hillmyer, M. A. Macromolecules 2012, 45, 4322-4332.
24. Lim, J.; Grove, B. C.; Roth, A.; Breaker, R. R. Angew. Chem. Int. Ed. 2006, 45, 6689-6693.
25. Olszewska, B.; Szulc, I.; Kryczka, B.; Kubiak, A.; Porwanski, S.; Zawisza, A. Tetrahedron: Asymmetry. 2013, 24, 212-216.
26. a) Viladoms, J.; Fedor, M. J. J. Am. Chem. Soc. 2012, 134, 19043-19049. b) Posakony, J. J.; Ferre-D’Amare, A. R. J. Org. Chem. 2013, 78, 4730-4743.
27. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2507.
28. Karkkainen, J.; Vihko, R. Carbohydr. Res. 1969, 10, 113-120.
29. Pothukanuri, S.; Winssinger, N. Org. Lett. 2007, 9, 2223-2225.
30. Kadam, S. T.; Kim, S. S. Green Chem. 2010, 12, 94-98.
31. Joseph, A. A.; Dhurandhare, V. M.; Chang, C.-W.; Verma,V. P.; V.; Mishra, P. G.; Ku, C.-C.; Lin, C.-C.; Wang, C.-C. Chem. Commun. 2015, 51, 104-106.
32. (a) Vasella, A.; Witzig, C.; Chiara, J.-L.; Martin-Lomas, M. Helv. Chim. Acta. 1991, 74, 2073-2077. (b) Nyffeler, P.T.; Liang, C. H.; Koeller, K. M.; Wong, C. H. . J. Am. Chem. Soc. 2002, 124, 10773-10778.
33. (a) Yan, R.-B.; Yang, F.; Wu, Y.; Zhang, L.-H.; Ye, X.-S. Tetrahedron Lett. 2005, 46, 8993-8995. (b) Ye, H.; Liu, R.; Li, D.; Liu, Y.; Yuan, H.; Guo, W.; Zhou, L.; Cao, X.; Tian, H.; Shen, J.; Wang, P. G. Org. Lett. 2013, 15, 18-21. (c) Masuko, S.; Bera, S.; Green, D. E.; Weïwer, M.; Liu, J.; De Angelis, P. L.; Linhardt, R. J. J. Org. Chem. 2012, 77, 1449-1456.
34. (a) Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Bassov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753. (b) Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis, 4th ed.; John Wiley & Sons: Hoboken, NJ, 2007.
35. Schriven, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
36. Ruff, J. K. Inorg. Chem. 1965, 4, 567-570.
37. Lu, K.-C.; Tseng S.-Y.; Lin, C.-C. Carbohydr. Res. 2002, 337, 755-760.
38. (a) Yu, C.-S.; Niikura, K.; Lin, C.-C.; Wong, C.-H. Angew. Chem., Int. Ed. 2001, 40, 2900-2903. (b) Lin, C.-C.; Lin, N.-P.; Sahabuddin, L. S. K.; Reddy, V. R.; Huang, L.-D.; Hwang, K. C.; Lin, C.-C. J. Org. Chem. 2010, 75, 4921-4928.
39. (a) Winkler, W. C.; Nahvi, A.; Roth, A.; Collins, J. A.; Breaker, R. R. Nature 2004, 428, 281-286. (b) Collins, J. A.; Irnov, I.; Baker, S.; Winkler, W. C. Genes Dev. 2007, 21, 3356-3368. (c) Ferre-D’Amare, A. R. Q. Rev. Biophys. 2010, 43, 423-447.
40. Gong, B.; Klein, D. J.; Ferre-D’Amare, A. R.; Carey, P. R. J. Am. Chem. Soc. 2011, 133, 14188-14191.
41. Klein, D. J.; Ferre-D’Amare, A. R. Science 2006, 313, 1752-1756.
42. (a) Hampel, K. J.; Tinsley, M. M. Biochemistry 2006, 45, 7861-7871. (b) Tinsley, R. A.; Furchak, J. R.; Walter, N. G. RNA. 2007, 13, 468-477.
43. (a) Cochrane, J. C.; Lipchock, S. V.; Strobel, S. A. Chem. Biol. 2007, 14, 97-105. (b) Klein, D. J.; Wilkinson, S. R.; Been, M. D.; Ferre-D’Amare, A. R. J. Mol. Biol. 2007, 373, 178-189.
44. Xin, Y.; Hamelberg, D. RNA. 2010, 16, 2455-2463.
45. (a) McCarthy, T. J.; Plog, M. A.; Floy, S. A.; Jansen, J. A.; Soukup, J. K.; Soukup, G. A. Chem. Biol. 2005, 12, 1221-1226. (b) Michael D. Been, Science 2006, 313, 1744-1745. (c) Viladoms, J.; Fedor, M. J. J. Am. Chem. Soc. 2012, 134, 19043-19049.
46. Anderson J. M.; Percival, E. Chem. and Ind. SS, 1954, 1018.
47. Maley, F.; Lardy, H. A. J. Am. Chem. Soc. 1956, 78, 1393-1397.
48. (a) Wong, C.-H.; Whitesides, G. M. J. Am. Chem. Soc. 1981, 103, 4890-4899. (b) Wong, C.-H.; Gordon, J.; Cooney, C. L.; Whitesides, G. M. J. Org. Chem. 1981, 46, 4676-4679.
49. Brown, D. H. Biochim. Biophys. Acta. 1951, 7, 487-493.
50. Chenault, H. K.; Mandes, R. F.; Hornberger, K. R. J. Org. Chem. 1997, 62, 331-336.
51. (a) Leloir, L. F.; Cardini, C. I. S. Biochim. et Biophys. Acta. 1953, 12, 15-22. (b) Pogell, B. M.; Gryder, R. M. J. Biol. Chem. 1957, 228, 701-712.

連結至畢業學校之論文網頁點我開啟連結
註: 此連結為研究生畢業學校所提供,不一定有電子全文可供下載,若連結有誤,請點選上方之〝勘誤回報〞功能,我們會盡快修正,謝謝!
QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top
系統版面圖檔 系統版面圖檔