臺灣博碩士論文加值系統

碳水化合物在許多生物機制中扮演非常重要的角色。化學合成是大量取得結構確定且具高純度的醣類分子的重要方式之一。然而，由於合成這些醣類分子時，不可避免的需要區分且選擇性的保護單醣上眾多的羥基，以及進行醣鏈結反應建立醣苷鍵時須面對的立體選擇性問題，以化學方式來合成這些醣類分子和其衍生物，對化學家而言是非常大的挑戰。
在本篇論文中，我們的目標是建立一個一鍋化組合式保護的策略，在單一反應瓶中進行多步化學反應，來區分並保護單醣單元上眾多的羥基。並利用得到的這些單醣單元，同樣以一鍋化的方式來合成��-1,6-葡聚糖和與禽流感病毒結合的寡醣分子庫。
在本篇論文的第一章中簡略的敘述了醣生物學的背景，第二章介紹製備單醣單元的傳統合成策略，第三章則回顧了傳統的醣鏈結反應以及最近文獻上一鍋化醣鏈結反應的進展。第四章所陳述的是本篇論文的目標，而第五章則詳細介紹了單醣一鍋化組合式保護的原理、反應條件、物理資料以及推測的反應機構。有上百個單醣單元從一個簡單的起始物開始，經由此一策略被有效率的合成出來。第六章則陳述了以這些單醣單元合成��-1,6-葡聚糖以及與禽流感病毒結合的寡醣分子庫的應用。而第七章敘述的是本論文簡單的總結。詳細的實驗步驟以及參考文獻則是分別陳述於第八章和第九章。

Carbohydrates are the key factors of many important biological processes. Chemical synthesis is one of the most practical ways to obtain the pure and structurally verified oligosaccharides. However, it is challenging for chemists, because of the inevitable regioselective protection of the polyhydroxyls and the stereoselective formation of every glycosidic bond.
In this thesis, we aim at the development of a combinatorial, regioselective, orthogonal and one-pot methodology for the regioselective protection of the individual hydroxyl group of a monosaccharide in a single reaction vessel, and the so formed building blocks are assembled into biologically important ��-1,6-glucans and influenza virus-binding trisaccharide library via a one-pot approach.
A brief introduction to the background of glycobiology is described in chapter 1. Chapter 2 presents the traditional strategies for the protection of various monosaccharides, and chapter 3 reviews the methods for the classical glycosylation reactions as well as the recent advances in one-pot sequential glycosylations. In chapter 4, the specific aims of this thesis are described. The principle, conditions, physical data and the proposed mechanisms for the one-pot protection of monosaccharide are described in chapter 5. Hundreds of building blocks could be efficiently synthesized starting form a simple sugar. Chapter 6 exhibits the applications to the one-pot synthesis�nof�n��-1,6-glucans and influenza virus-binding trisaccharide library, and a brief conclusion is summarized in chapter 7. The detail experimental section and a list of references are described in chapters 8 and 9, respectively.

Content
Abstract i
摘要 ii
Acknowledgments iii
Abbreviations iv
Content x
Chapter 1: Introduction of Carbohydrates 1
Chapter 2: Literature Survey for the Protection of Carbohydrates 10
2.1. Differentiation of primary alcohols using bulky protecting groups 13
2.2. Protection of diols using acetal protecting groups. 17
2.3. Conversion of hexopyranoses into 1,6-anhydro derivatives 30
2.4 Summary 36
Chapter 3: Literature Survey for Traditional and One-pot Glycosylation 37
3.1. Brief introduction of glycosyl donors and their corresponding promoters. 39
3.1.1. Glycosyl bromide and chloride. 40
3.1.2. Glycosyl fluoride. 40
3.1.3. Thioglycoside. 41
3.1.4. Glycosyl sulfoxides. 44
3.1.5. Selenoglycosides. 44
3.1.6. Glycosyl imidates. 45
3.1.7. Glycosyl phosphite. 46
3.1.8. Glycosyl phosphate. 47
3.1.9. n-Pentenyl glycoside and glycosyl 4-pentenoate. 47
3.1.10. Direct glycosylation with 1-hydroxyl donors 48
3.2. The effect of protecting groups. 49
3.3. The effect of the conformation of donors and acceptors 50
3.4. The effect of temperature. 51
3.5. The effect of solvent. 52
3.6. One-pot glycosylation (OPG) for the synthesis of oligosaccharides. 52
3.6.1. Armed-disarmed strategy 54
3.6.2. Orthogonal leaving group strategy 58
3.6.3. Distinguishable acceptors strategy 61
3.6.4. Hybrid of the previously described strategy 63
3.6.5. The preactivation strategy 64
Chapter 4: Specific Aims 67
Chapter 5: Results and Discussion for One-pot Protection 69
5.1. One-pot synthesis of 2-alcohols 72
5.2. One-pot synthesis of fully protected glycosides 75
5.3. One-pot synthesis of O3 alocohols 81
5.4. One-pot synthesis of the fully protected monosaccharides 82
5.5. One-pot synthesis of 3-alcohols 84
5.6. One-pot synthesis of 4-alcohols 86
5.7. One-pot synthesis of 6-alcohols 90
5.8. Summary 92
5.9. Mechanisms 93
Chapter 6: Results and discussion for one-pot glycosylation 96
���|���|�n�積e-pot synthesis of ��-1,6-glucans 96
6.2. One-pot synthesis of influenza virus-binding trisaccharide on human host 102
Chapter 7: Conclusion 115
Chapter 8: Experimental Section 118
Chapter 9: References 219
Appendix 232

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