1,1,1,3,3,3-Hexamethyldisilazane (HMDS) Trimethylsilylation of Alcohols for Concise Carbohydrate Synthesis

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研究生：	亞洛克 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 Lin, Chun-Cheng 王正中 Wang, Cheng-Chung
口試委員:	蒙國光 Mong, Kwok Kong Tony 洪上程 Hung, Shang-Cheng 汪炳鈞 Uang, Biing-Jiun 王聖凱 Wang, Sheng-Kai
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
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：	HMDS, Silylation, Phosphorylation, Trehalose desymmetrization
相關次數：	點閱：2 下載：0
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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

                                

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