| Description |
1 online resource. |
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text txt rdacontent |
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computer c rdamedia |
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online resource cr rdacarrier |
| Summary |
Synthetic Strategies in Carbohydrate Chemistry covers carbohydrate synthesis and its widespread application in various disciplines including catalysis. Basic and advanced aspects of carbohydrates are covered, starting with a brief introduction and then followed by protection-deprotection strategies in carbohydrate chemistry, glycosidic bond formation methodology, and their impact in oligosaccharide synthesis. Recent synthetic approaches for O-glycosides, N-glycosides, thioglycosides and C-glycosides, Intramolecular Aglycon Delivery (IAD), and carbohydrate modification are discussed, as well as stereoelectronic factors that control the chemical and biochemical behavior of carbohydrates in living cells. In addition, diverse applications of synthetic carbohydrate chemistry are covered, including sugar-based chiral catalyst in stereoselective synthesis, sugar-based ionic liquids, one-pot tandem reactions in carbohydrates, total synthesis of glycoconjugated natural products, impact of sugar in drug discovery and development, vaccine development, and glycoengineering. This reference is essential reading for researchers working in synthetic carbohydrate chemistry and biochemistry, and will be useful to those working in total synthesis, novel synthetic methodology, catalysis, polymer science, glycobiology, medicinal chemistry, and process development chemistry. |
| Note |
Includes index. |
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Print version record. |
| Contents |
Front Cover -- Synthetic Strategies in Carbohydrate Chemistry -- Copyright Page -- Contents -- List of contributors -- Foreword -- Preface -- List of abbreviations -- 1 Glycosidic bond formation methodology: challenges and impact in oligosaccharide synthesis -- 1.1 Introduction -- 1.2 Complexity of carbohydrates -- 1.3 General aspects of oligosaccharide synthesis -- 1.3.1 Anomeric effect -- 1.3.2 Background on classical approaches -- 1.3.3 Mechanistic studies -- 1.3.3.1 Armed-disarmed approach -- 1.3.3.2 Active-latent glycosylation -- 1.3.3.3 Remote participation |
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1.4 Glycosylation reactions -- 1.4.1 Glycosyl donors -- 1.4.1.1 Glycosyl chlorides and bromides -- 1.4.1.2 Glycosyl iodides -- 1.4.1.3 Glycosyl fluorides -- 1.4.1.4 Thioglycosides -- 1.4.1.5 Glycosyl trichloroacetimidates -- 1.4.2 Role of acceptors -- 1.5 Conclusions and future outlook -- References -- 2 Recent advances in stereoselective intramolecular O-glycosylation -- 2.1 Introduction -- 2.2 Molecular clamping approach -- 2.3 Intramolecular aglycon delivery concept -- 2.4 Leaving group approach -- 2.5 Conclusions and future outlook -- Acknowledgments -- References |
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3 Thioglycoside-based glycosylations in oligosaccharide synthesis -- 3.1 Introduction -- 3.2 Preparation of thioglycosides -- 3.2.1 One-pot synthesis of thioglycosides from unprotected sugars -- 3.3 Activation of thioglycoside donors with various promoters -- 3.4 Thioglycosides for chemoselective glycosylations -- 3.4.1 Type A chemoselective glycosylations -- 3.4.2 Type B chemoselective glycosylations -- 3.4.3 Type C chemoselective glycosylations -- 3.4.4 One-pot chemoselective glycosylations -- 3.5 Orthogonal glycosylations |
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3.5.1 Orthogonal glycosylations of thioglycoside acceptors with halide glycosyl donors -- 3.5.2 Orthogonal glycosylations between trichloroacetimidate donors and thioglycoside acceptors -- 3.5.3 Orthogonal coupling of thioglycoside acceptors with N-phenyltrifluoroacetimidate donors -- 3.5.4 Orthogonal glycosylations of thioglycoside acceptors with other glycosyl donors -- 3.5.5 Thioglycoside-based one-pot orthogonal glycosylations -- 3.6 Preactivation-based glycosylation strategies -- 3.6.1 Preactivation glycosylations based on the AgOTf/p-ArSCl promoter system |
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3.6.2 Preactivation-based one-pot glycosylations -- 3.7 Summary and future outlook -- References -- 4 General strategy for the synthesis of N-glycosides -- 4.1 Introduction -- 4.2 Nucleosides and their derivatives found in nature -- 4.3 General strategy for the chemical synthesis of nucleosides and other N-glycosides -- 4.3.1 Chemical synthesis of nucleosides via N-glycosylation -- 4.3.1.1 Glycosyl acetates -- 4.3.1.2 Glycosyl halide -- 4.3.1.3 Thioglycosides -- 4.3.1.4 Anhydroses -- 4.3.1.5 Pentenyl glycosides -- 4.3.1.6 Propargyl-1,2-orthoesters -- 4.3.1.7 Glycosyl ortho-hexynylbenzoates |
| Subject |
Carbohydrates -- Synthesis.
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Glucides -- Synthèse.
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| Added Author |
Tiwari, Vinod Kumar, editor.
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| Other Form: |
Print version: SYNTHETIC STRATEGIES IN CARBOHYDRATE CHEMISTRY. [S.l.] : ELSEVIER - HEALTH SCIENCE, 2023 0323917291 (OCoLC)1370924332 |
| ISBN |
9780323917292 |
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9780323986496 (electronic bk.) |
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0323986498 (electronic bk.) |
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0323917291 |
| Standard No. |
AU@ 000075321079 |
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AU@ 000075360845 |
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AU@ 000075370804 |
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