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Elsevier

The Chemistry of C-Glycosides

  • 1st Edition, Volume 13 - December 1, 1995
  • Latest edition
  • Editors: D.E. Levy, C. Tang
  • Language: English

In recent years C-glycoside chemistry has been one of the main topics in carbohydrate chemistry, not only because of the synthetic challenges posed, but also because C-glyc… Read more

Description

In recent years C-glycoside chemistry has been one of the main topics in carbohydrate chemistry, not only because of the synthetic challenges posed, but also because C-glycosides have the potential to serve as carbohydrate analogues resistant to metabolic processes. Consequently, this class of compounds is currently receiving much interest as a potential source of therapeutic agents for clinical use. This book provides a broad coverage of the various synthetic methods available for the preparation of C-glycosides, and illustrates the interesting breadth of connections between carbohydrate chemistry and modern general synthetic organic chemistry by including topics such as transition-metal catalysis, radical chemistry, cycloaddition and rearrangement processes. In addition, in the final chapter of the book, the syntheses of C-di and trisaccharides reported through 1994 are reviewed. This well organised account of the synthetic chemistry in this field will prove to be very valuable to a wide range of researchers and advanced students, both as an introduction to the topic and for reference.

Readership

For organic chemists, medicinal chemists, graduate students and academic and industrial researchers

Table of contents

Introduction
Organization of the book. Definition and nomenclature of C-Glycosides. O-Glycosides vs C-Glycosides: comparisons of physical properties, anomeric effects, H-bonding abilities, stabilities and conformations. Natural occurring C-Glycosides. C-Glycosides as stable pharmacophores. Further reading. References.

Electrophilic Substitutions
Introduction. Anomeric activating groups and stereoselectivity. Cyanation reactions. Alkylation, allenylation, allylation and alkynation reactions. Arylation reactions. Reactions with enol ethers, silylenol ethers and enamines. Nitroalkylation reactions. Reactions with allylic ethers. Wittig reactions with lactols. Nucleophilic additions to sugar lactones followed by lactol reductions. Nucleophilic additions to sugars containing enones. Transition metal mediated carbon monoxide insertions. Reactions involving anomeric carbenes. Reactions involving exoanomeric methylenes. References
Nucleophilic Sugar Substitutions
Introduction. C1 lithiated anomeric carbanions by direct metal exchange. C1 lithiated anomeric carbanions by reduction. C1 carbanions stabilized by sulfones, sulfoxides, carboxyl and nitro groups. References

Transition Metal Mediated C-Glycosidations
Introduction. Direct coupling of glycals with aryl groups. Coupling of substituted glycals with aryl groups. Coupling of &pgr;-allyl complexes of glycals. Mechanistic considerations. References

Anomeric Radicals
Introduction. Sources of anomeric radicals and stereochemical consequences. Anomeric couplings with radical acceptors. Intramolecular radical reactions. References

Rearrangements and Cycloadditions
Introduction. Rearrangements by substituent cleavage and recombination. Electrocyclic rearrangements involving glycals. Rearrangements from the 2-hydroxyl group. Biomolecular cycloadditions. Manipulations of C-Glycosides. References

Sugar Ring Formations
Introduction. Wittig reactions of lactols followed by ring closures. Addition of Grignard and organozinc reagents to lactols. Cyclization of suitably substituted polyols. Rearrangements. Cycloadditions. Other methods for the formation of sugar rings. References

Syntheses of C-Di and Trisaccharides
Introduction. Syntheses reported in 1983. Syntheses reported in 1984. Syntheses reported in 1985. Syntheses reported in 1986. Syntheses reported in 1987. Syntheses reported in 1988. Syntheses reported in 1989. Syntheses reported in 1990. Syntheses reported in 1991. Syntheses reported in 1992. Syntheses reported in 1993. Syntheses reported in 1994. Trends of the future. References. Index.

Review quotes

"This is a monumental work that provides essentially comprehensive coverage of C-gylcosides. This book shows various synthetic methods available for the preparation of C-glycosides, and illustrates the interesting breadth of connections between carbohydrate chemistry and modern general synthetic organic chemistry....It should become an important companion for both graduate students and senior researchers in the field."—Heterocycles

"The book discusses the chemistry of C-glycosides in eight chapters....The following reaction types are covered: electrophilic substitutions, nucleophilic substitutions, transition metal mediated C-glycosylations, anomeric radicals, rearrangements and cycloadditions, and sugar ring formations....In summary, the book is well presented and gives a comprehensive Review of the subject. It should be of interest to a wide audience."—Chemistry and Industry

"This book, like others in the Tetrahedron Organic Chemistry Series, represents a timely Review of the rapidly burgeoning field in carbohydrate chemistry. The emphasis of this book is on the synthetic perspective of C-glycosides....The book is concisely written and the schemes are neatly drawn. Graduate students and researchers interested in organic synthesis related to carbohydrates will find this useful, as the book serves an excellent introductory overview of the subject it covers....This reviewer recommends this book enthusiastically."—Synthesis

Product details

  • Edition: 1
  • Latest edition
  • Volume: 13
  • Published: December 21, 1995
  • Language: English

About the editors

DL

D.E. Levy

Affiliations and expertise
Glycomed Inc., California, USA

CT

C. Tang

Dr. Tang is a professor at the Department of Food Science and Technology of South China University of Technology. He holds a Bachelor of Science degree in Food Science and Technology from Zhejiang University of Technology, China and obtained a Master in Food Engineering from Wuxi University of Light Industry, and a doctorate (Ph.D.) in Food Science from South China University of Technology. Professor Tang has conducted almost 20 years of research in the areas including food science, food colloids, functional foods and protein-based materials, especially those related to plant proteins. His recent research interests include structure and functionality of plant protein chemistry, development and novel applications of plant protein-stabilized emulsions, and nanoencapsulation of bioactives. In these areas, he has published more than 140 papers and edited two books. Currently he serves as an associate editor of several journals, including Food Research International (Elsevier) and Journal of Integrative Agriculture (Elsevier).
Affiliations and expertise
Professor, Department of Food Science and Technology, South China University of Technology, Guangzhou South China

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