C-Glycoside Synthesis: 1st Edition (Hardback) book cover

C-Glycoside Synthesis

1st Edition

By Maarten Postema

CRC Press

400 pages

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Hardback: 9780849391507
pub: 1995-02-14
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Description

This book examines methods particularly well suited for either a- or b-C-glycoside formation. It helps field workers quickly select the best method for synthesizing a particular type of C-glycoside. The use of C-glycosides as synthons in natural product synthesis is also addressed.

Reviews

"The author is to be congratulated for drawing together these new developments in an extremely comprehensive way."

-J. Carbohydrate Chem., 15 (1), January 1996

Table of Contents

Electrophilic Sugars in C-Glycoside Synthesis I

Introduction

Lactols

O-Glycosides

S-Glycosides

Anomeric O-Trichloroacetimidates

Anomeric Acetates

Glycosyl Halides

References

Electrophilic Sugars in C-Glycoside Synthesis II

Introduction

Glycals

Enitols and Anhydro Sugars

Lactones

Intramolecular Arylation

Conclusion

References

C-1 Nucleophiles in C-Glycoside Preparation

Introduction

C-1 Stabilized Anions

Anomeric Anions

Transition Metal Anomeric Complexes

C-1 Vinyl Anions

Conclusion

References

Wittig Approaches to C-Glycoside Formation

Introduction

Use of Stabilized Phosphoranes

Horner-Wadsworth-Emmons Approaches

Olefination Followed by Electrophilic Cyclization

Use of Sulfur Ylides

Olefination of Sugar Lactones

Conclusion

References

Palladium Mediated Approaches to C-Glycosides

Introduction

p-Allyl Complexes

Heck Type Couplings

Conclusion

References

Concerted Reactions Applied to C-Glycoside Preparation

Introduction

Sigmatropic Rearrangements

Cycloadditions

Conclusion

References

Free Radical Approaches to C-Glycosides

Introduction

Intermolecular Additions

Intramolecular Approaches

Anomeric Carbenes

Conclusion

References

C-Disaccharide Synthesis

Introduction

Synthetic Approaches to C-Disaccharides

Synthetic Approaches to C-Trisaccharides

Conclusion

References

Some Naturally Occurring Alkyl C-Glycosides

Introduction

Alkyl C-Pyranoside Natural Products

Alkyl C-Furanoside Natural Products

Conclusion

References

Synthesis of Naturally Occurring Aryl C-Glycosides

Introduction

Aryl C-Glycoside Natural Products

Conclusion

References

C-Nucleoside Synthesis

Biologically Relevant C-Nucleosides

Synthetic Approaches to C-Nucleosides

Conclusion

References

Biological and Practical Applications of C-Glycosides

Introduction

Biological Applications

Other Applications

Conclusion

References

Index

About the Series

New Directions in Organic & Biological Chemistry

Learn more…

Subject Categories

BISAC Subject Codes/Headings:
MED008000
MEDICAL / Biochemistry
SCI013050
SCIENCE / Chemistry / Physical & Theoretical