Synthetic Strategies in Carbohydrate Chemistry

1st Edition - October 26, 2023
Editor: Vinod Kumar Tiwari
Language: English
Paperback ISBN:
9 7 8 - 0 - 3 2 3 - 9 1 7 2 9 - 2
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 9 8 6 4 9 - 6

Synthetic Strategies in Carbohydrate Chemistry covers carbohydrate synthesis and its widespread application in various disciplines including catalysis. Basic and advanced aspects o… Read more

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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.

Cover image
Title page
Table of Contents
Copyright
List of contributors
Foreword
Preface
List of abbreviations
Chapter 1. Glycosidic bond formation methodology: challenges and impact in oligosaccharide synthesis
Abstract
1.1 Introduction
1.2 Complexity of carbohydrates
1.3 General aspects of oligosaccharide synthesis
1.4 Glycosylation reactions
1.5 Conclusions and future outlook
References
Chapter 2. Recent advances in stereoselective intramolecular O-glycosylation
Abstract
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
Chapter 3. Thioglycoside-based glycosylations in oligosaccharide synthesis
Abstract
3.1 Introduction
3.2 Preparation of thioglycosides
3.3 Activation of thioglycoside donors with various promoters
3.4 Thioglycosides for chemoselective glycosylations
3.5 Orthogonal glycosylations
3.6 Preactivation-based glycosylation strategies
3.7 Summary and future outlook
References
Chapter 4. General strategy for the synthesis of N-glycosides
Abstract
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
4.4 Conclusions and future outlook
Acknowledgments
References
Chapter 5. The emerging polyhydroxyazepane-based C-glycosides for glycosidase inhibition
Abstract
5.1 Introduction
5.2 Piperidine-based iminosugars as glycosidase inhibitors: background
5.3 The emergence of polyhydroxyazepanes
5.4 Emerging C-glycosides of polyhydroxyazepanes
5.5 Conclusions and future outlook
References
Chapter 6. Sialic acid donors: stereoselective chemical and enzymatic O-glycosylations
Abstract
6.1 Introduction
6.2 Some notable characteristics of sialic acids
6.3 Common approaches in chemical sialylation
6.4 Conclusions and future outlook
Acknowledgments
References
Chapter 7. Common protection–deprotection strategies in carbohydrate synthesis
Abstract
7.1 Introduction
7.2 Common protection–deprotection strategies
7.3 Conclusions and future outlook
References
Chapter 8. Synthetic chemistry of D-fructose
Abstract
8.1 Introduction
8.2 D-Fructose in synthetic chemistry
8.3 L-Sorbose in synthetic chemistry
8.4 Conclusion and future prospective
Acknowledgments
References
Chapter 9. Recent synthetic strategies to access diverse iminosugars
Abstract
9.1 Introduction
9.2 Monocyclic iminosugars
9.3 Bicyclic iminosugars
9.4 Conclusions and future outlook
References
Chapter 10. Vinyl sugar enol ethers in organic synthesis
Abstract
10.1 Introduction
10.2 Synthesis and reactivity of pyranoid glycals
10.3 Synthesis and reactivity of furanoid glycals
10.4 Conclusions and future outlook
References
Chapter 11. Synthesis of carbohydrate-containing macrocycles
Abstract
11.1 Introduction
11.2 Natural product-based glycomacrocycles
11.3 Sugar-based crown ether, azacrown ether, and other crown ether-like macrocycles
11.4 Synthesis of macrocycles by C–C bond forming reactions
11.5 Synthesis of sugar-embedded macrocycles by reductive amination, macrolactamization, and macrolactonization
11.6 Synthesis of macrocycles via click macrocyclizations
11.7 Conclusion and future perspective
Acknowledgement
References
Chapter 12. Recent advances in synthesis of diverse glycopeptides and glycohybrids
Abstract
12.1 Introduction
12.2 Synthesis of O-linked glycopeptides
12.3 Synthesis of S-linked glycopeptides
12.4 Synthesis of C-linked glycopeptides
12.5 Synthesis of N-linked glycopeptides
12.6 Recent developments for the synthesis of glycohybrids
12.7 Conclusions and future outlook
References
Chapter 13. Carbohydrate-based chiral organocatalysts
Abstract
13.1 Introduction
13.2 Organocatalysts: historical background and basic aspects
13.3 Carbohydrates as potent scaffolds for organocatalysis
13.4 Carbohydrate-based ketones: organocatalysts for enantioselective epoxidation
13.5 Carbohydrate-based prolinamides, pyrrolidine amides and pyrrolidines: organocatalysts for aldol and Michael reactions
13.6 Carbohydrate-derived amino alcohols: organocatalysts for asymmetric aldol and Mannich reactions
13.7 Carbohydrate-based thiourea amines: bifunctional organocatalysts for Michael, Biginelli, aza-Henry, and Mannich reactions
13.8 Other organocatalysts derived from carbohydrates
13.9 Conclusions and future outlook
References
Chapter 14. Emerging aspects of domino reactions in carbohydrate Chemistry
Abstract
14.1 Introduction
14.2 Asymmetric tandem reactions using chiral carbohydrate derivatives
14.3 Organocatalyzed tandem reaction
14.4 Glycals in domino reaction
14.5 Reductive ring opening in tandem reactions of carbohydrates
14.6 Miscellaneous examples
14.7 Conclusions and future outlooks
Acknowledgments
References
Index

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Synthetic Strategies in Carbohydrate Chemistry

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Vinod Kumar Tiwari