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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 王正中 | |
dc.contributor.author | Chun-Wei Chang | en |
dc.contributor.author | 張峻瑋 | zh_TW |
dc.date.accessioned | 2021-06-17T09:08:11Z | - |
dc.date.available | 2029-12-31 | |
dc.date.copyright | 2019-12-02 | |
dc.date.issued | 2019 | |
dc.date.submitted | 2019-11-19 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/74819 | - |
dc.description.abstract | 在化學合成醣類衍生物時,立體選擇性、位向選擇性以及產率皆為醣鏈結反應中重要的環節,然而,儘管在這數十年來許多文獻已記載了許多可能的解決方向,這些合成上的困境依然無法有效解決。在本論文中,我們首度發現立體選擇性醣鏈結可以利用醣予體的活性進行快速預測,而反應機構的探討更結論出醣基碘化物以及醣基三氟甲磺酸化物這兩種截然不同的中間產物主導著整個醣鏈結反應,雖然不同比例的醣基中間體劇烈的影響反應之選擇性,本論文已有效的歸納和整合其分子行為。除此之外,透過相對反應數值以及統計上的分析,我們首次量化醇類分子在酸性條件下的活性,並且有效的定義出醣鏈結反應之趨勢和高產率區間。最後,我們成功建構出一個數學方程式來預測醣鏈結反應之結果,此方程式涵蓋眾多重要的變因,包括不同活性的醣予體、醣受體、溶劑、離去基、以及啟動子。此預測系統不但具備了高準確性,也可幫助我們在簡潔的步驟中高效地合成出一系列的醣類衍生物。 | zh_TW |
dc.description.abstract | Stereoselectivity, regioselectivity and reaction yield are paramount for successful glycosylation reactions, which are key to the chemical synthesis of glycoconjugates. However, achieving them has remained a major challenge for many decades despite the significant efforts documented in the literature. To rationalize our discovery, in this thesis, we have discovered that the stereoselective outcome can be predicted by sugar reactivity with a defined relative reactivity value (RRV). Our mechanism studies also concluded that reaction was dominated by two distinct intermediates, glycosyl triflate and glycosyl iodide. The relative quantities of glycosyl triflate to iodide greatly influence the stereoselectivity, and glycosyl intermediate’s behavior was clarified in this work. The RRV of acceptors (ARRV) is designed to indicate the reactivity of an alcohol under acidic condition for the first time. A trend for the yields and a guideline for high-yielding reactions can also be defined based on RRV-ARRV, using a statistical approach. The equation has involved numerous crucial factors, such as donor and acceptor reactivity, solvent polarity, the leaving group and the promotor. Many carbohydrate-based derivatives can be efficiently synthesized in concise steps with high accuracy. | en |
dc.description.provenance | Made available in DSpace on 2021-06-17T09:08:11Z (GMT). No. of bitstreams: 1 ntu-108-D03223207-1.pdf: 25319116 bytes, checksum: 94e2d7cc202617ba58b23cd5effe0345 (MD5) Previous issue date: 2019 | en |
dc.description.tableofcontents | Chapter 1 Introduction 1
1.1 Glycolysis metabolic pathway 1 1.2 The definition of carbohydrate and glycosylation 3 1.2.1 The structure of carbohydrate 3 1.2.2 Carbohydrate-active enzymes 5 1.2.3 Inverting glycosidase and retaining glycosidase 6 1.2.4 The definition of glycoprotein 7 1.3 Regioselective one-pot protection of carbohydrate organic synthesis 10 1.3.1 A highly efficient TMSOTf‐catalyzed HMDS silylation of sugars 12 1.3.2 Regioselective one-pot functionalization from free sugars 12 1.3.3 Chemoselective N-functionalization from glucosamine 14 1.3.4 Regioselective one-pot protection for thioglycoside derivatives 15 1.4 The overview of chemical glycosylation 18 1.5 Characters of the glycosyl donor 20 1.5.1 Glycosyl halide 20 1.5.2 Glycosyl acetate 21 1.5.3 Thioglycoside 21 1.5.4 Glycosyl imidate 22 1.5.5 The reported works of glycosyl halide 23 1.5.6 The reported works of glycosyl imidate 28 1.5.7 The reported works of thioglycoside 32 1.6 The reaction yields depended on the nucleophilicities of the acceptor 42 1.6.1 Different protecting groups on acceptor influence glycosylation yield 42 1.6.2 A comparative study of protecting group effect on acceptors 43 1.6.3 A competitive reaction of the electronic effect on the acceptor 45 1.7 Stereoselective glycosylation 47 1.7.1 Solvent effect 47 1.7.2 Neighboring group participation 48 1.7.3 Remote-controlled glycosylation 48 1.7.4 Conformationally controlled glycosylation 49 1.7.5 Two-step indirect β-mannosylation 49 1.7.6 The reaction mechanism on the formation of α- and β-glycoside 50 1.7.7 The experimental evidence in support of the glycosylation mechanism 51 Chapter 2. An indicator-assisted control for glycosylation reactions 65 2.1 Preparation of glycosyl donors with defined RRV 65 2.2 RRV as an indicator of stereoselectivity 66 2.3 The general guideline for stereocontrolled glycosylation 70 2.4 The identification of glycosyl intermediate 72 2.5 RRV as an indicator for intermediate ratio 75 2.6 Computational calculation 79 2.7 Stereoselectivity-predictable glycosylation using RRV as the indicator 94 Chapter 3 Mechanism studies in NIS/TfOH system 97 3.1 Proposed mechanism on the formation of glycosyl iodide intermediate 98 3.2 Intermediate-controlled glycosylation using reagent dosage 98 3.3 The verification of TolSI participation for selective α-glycosylation 100 3.4 The mechanistic studies 102 3.5 The observation of intermediate transformation 103 3.6 The mechanism in the NIS/TfOH system 106 Chapter 4. The GlycoComputer: explorer for chemical glycosylation 108 4.1 Relative reactivity value of donors (RRV) 109 4.2 Experimental design for Aka experiments 110 4.3 Relative reactivity value of acceptors (Aka) 112 4.4 Correlation of RRV and Aka with the stereoselectivity in glycosylation 114 4.5 A mathematic formula exploring the promotor effect 115 4.6 A mathematic formula exploring solvent effects 128 4.7 The general mathematic formula 129 4.8 The association of reaction yield 130 4.9 Synthetic glycosylation reactions of Lewis A trisaccharides 131 Chapter 5. Conclusion 136 Chapter 6. Experimental section and NMR spectra 138 6.1 General procedure 138 6.2 General procedure for RRV experiment of thioglycosides 138 6.3 Synthetic procedure for donors 138, 266-280 139 6.4 Detailed results of computational study 189 6.5 Detail protocol in the determination of Aka 192 6.6 Glycosylation reactions in NIS/TfOH System 195 Chapter 7. References 237 Chapter 8. Publications 248 Chapter 9. Spectra 264 | |
dc.language.iso | en | |
dc.title | 以反應性定量建立醣鏈結反應及其中間產物之演算法 | zh_TW |
dc.title | Establishment of an Algorithm for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity | en |
dc.type | Thesis | |
dc.date.schoolyear | 108-1 | |
dc.description.degree | 博士 | |
dc.contributor.coadvisor | 吳世雄 | |
dc.contributor.oralexamcommittee | 洪上程,羅順原,Todd L. Lowary,許昭萍 | |
dc.subject.keyword | 立體選擇,醣鏈結反應,反應機構探討探, | zh_TW |
dc.subject.keyword | Glycosylation, | en |
dc.relation.page | 366 | |
dc.identifier.doi | 10.6342/NTU201904294 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2019-11-19 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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