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研究生:吳旭軒
研究生(外文):Hsu-Hsuan Wu
論文名稱:(1)設計並合成Acaterin及其衍生物、(2)Endo-Glycals立體選擇性之醣加成反應
論文名稱(外文):(1) Design and synthesis of (-)-Acaterin derivatives 、(2) Stereoselective Glycosylation of endo-Glycals
指導教授:林煇章
學位類別:碩士
校院名稱:中國醫藥大學
系所名稱:藥物化學研究所碩士班
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:152
中文關鍵詞:乙醯基轉移酶抑制劑醣加成反應
外文關鍵詞:Acaterin2-deoxy glycosidesbeta-enamino ketones
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目標化合物Acaterin (1)的合成可大致分為兩個片段,利用市售藥品Methyl acrylate與甲醛進行Baylis-Hillman反應得到第一片段,同時也用Methyl (S)-(-)-lactate進行Wittig反應得到第二片段;而本實驗室已將兩片段合成出,目前正進行Mitsunobu反應以及Grubbs catalyst將此兩片段接合起來,來得到Acaterin的內酯。
此外,根據文獻報導,目前新方法合成2-deoxy glycosides是由hex-1-en-3-uloses當作起始物,利用路易士酸為催化而得;而本實驗室利用AlCl3?n當作催化劑,在微波反應條件下,可得到高產率、高立體選擇性的2-deoxy glycosides,同時???n: ???n的比例超過?n???~?n???n?﹛C
最後,本實驗將endo-glycal利用PhI(OH)OTs氧化試劑得到開環產物,並且利用一鍋化反應,同時加入胺類,來得到??-enamino ketones。
The intermediate compounds was synthesized by Baylis-Hillman reaction to couple acetaldehyde and the compound 13. We also used the starting compound 27 followed by reduction and Wittig rection to affored the intermediate compounds (E)-46, (Z)-46. The further works will be finished by Mitsunobu and Grubbs catalysis reaction to give to major compound 23.
A new method for synthesis of ??-2-deoxyglycosides from hex-1-en-3-uloses is reported, hex-1-en-3-uloses were shown to be efficient glycosyl donors by using catalyst amount of AlCl3 in microwave-assisted glycosylation. In these reaction ??-glycosyl additions occurred with highly stereoselectivity (??:??=10:1).
Fully protected endo-glucals are directly converted into compound 104, 105 by 1eq PhI(OH)OTs, followind addition amino in methanol at room temperature for 30 mins to affored the ??-enamino ketones.This sequestration reaction occurs in two steps which were studied separately and in a one-pot rection.
<第一部分>
Design and synthesis of (-)-Acaterin derivatives
中文摘要………………………………………………………………2
英文摘要………………………………………………………………3
第一章 緒論…………………………………………………………4
1.1 研究概況.................................…………………..……………..4
第二章 研究目的與動機…………………………………………..11
第三章 結果與討論………………………………………………..13
3.1 化合物1的合成策略及步驟……………………………….13
3.2 化合物31之合成步驟………………………………………...13
3.3 化合物1之新合成策略及步驟………………………………15
3.4 化合物26之合成步驟…………….………………………...16
3.5 化合物25之合成步驟…………….…….…………………18
3.6 化合物23之合成步驟…………….…….…………………22
3.7 化合物1之合成步驟…………….…….…………………23
第四章 結論………………………………………………………..25
<第二部分>
Stereoselective Glycosylation of endo-Glycals
第一章 緒論………………………………………………….27
1.1 研究概況.................................…………………..………27
第二章 研究目的與動機…………………………………………..36
第三章 結果與討論………………………………………………..37
3.1 2-deoxyglycosides類緣物之合成……………….……….37
3.2 ??-enamino ketones的合成策略……………………………..42
第四章 結論………………………………………………………..49
第五章 實驗部分…………………………………………………..50
5.1 試藥、溶媒及材料..……………………...……………..……..50
5.2 重要儀器…..…………………………………………….……54
5.3 化合物的製備…..……………………………….……………58
參考文獻………………………………………………………………102
附錄(圖譜部分)…………………………………………………….110
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