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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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Request a sales quoteSynthetic 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.
- Presents a practical and detailed overview on glycosylation methodology
- Covers automated glycosylation strategies in glycan synthesis
- Includes recent progress in the synthesis and significance of diverse thio-glycosides, C-glycosides, imino sugars and carbasugars
- Highlights the impact of enzymes in glycan synthesis
- Discusses the recent approaches for the synthesis of neoglycoconjugates
Researchers working in the area of synthetic carbohydrate chemistry and biochemistry
- 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
- No. of pages: 768
- Language: English
- Edition: 1
- Published: October 26, 2023
- Imprint: Elsevier
- Paperback ISBN: 9780323917292
- eBook ISBN: 9780323986496
VT
Vinod Kumar Tiwari
Dr. Vinod K. Tiwari is Professor of Organic Chemistry at Banaras Hindu University. His teaching interest covers almost all branches of organic chemistry, and his research interest is highly focused on ‘Synthetic Carbohydrate Chemistry’. With more than 21 years of research and 17 years of teaching experience, Dr. Tiwari has supervised twelve PhD theses, twenty MS dissertations and contributed significantly to 150 peer-reviewed publications, several patents and invited book chapters of high repute. Dr. Tiwari's research has received many prestigious awards. He is an editorial board member of Trends Carbohydrate Res, Current Organic Chemistry, ARKIVOC, and J. Chem., and holds the Secretary position at the Association of Carbohydrate Chemist & Technologists, India. Recently, Dr. Tiwari edited a book Carbohydrates in Drug Discovery and Development for Elsevier.
Affiliations and expertise
Professor of Organic Chemistry, Banaras Hindu University, Varanasi, India