C-Furanosides - 1st Edition - ISBN: 9780128037393

C-Furanosides

1st Edition

Synthesis and Stereochemistry

Authors: Peter Goekjian Arnaud Haudrechy Boudjema Menhour Claire Coiffier
Paperback ISBN: 9780128037393
Imprint: Academic Press
Published Date: 14th December 2017
Page Count: 794
Tax/VAT will be calculated at check-out Price includes VAT (GST)

Institutional Access

Secure Checkout

Personal information is secured with SSL technology.

Free Shipping

Free global shipping
No minimum order.

Description

C-Furanosides: Synthesis and Stereochemistry provides a much needed overview of synthetic and stereochemical principles for C-pentofuranosides: analogs of a 5-membered ring carbohydrate glycoside (furanoside), in which the anomeric oxygen has been replaced with a carbon.

Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological applications, as conformational probes, or for biological studies.

While our understanding of conformational behavior and of stereoselective synthesis in 6-membered ring compounds is quite good, our ability to predict the conformation of 5-membered ring compounds, or to predict the stereochemical outcome of a given reaction remains anecdotal, and even the famous anomeric effect is poorly understood in 5-membered rings.

Through a comprehensive review of literature approaches to the different C-furanoside stereoisomers, as well as an interpretation of the outcome in terms of a reasonable number of stereochemical models, this book enables the reader to determine the best approach to a particular C-glycoside compound, also helping them gain an understanding of rationalization and predictability for the synthesis of new systems.

Key Features

  • Focuses on the chemistry of bioactive natural products
  • Contains contributions by leading authorities in the field
  • Presents sources of new pharmacophores

Readership

Organic, natural product, and carbohydrate chemists in industry and academia

Table of Contents

Part A: Introduction on C-Glycosides of Lyxose and Ribose
1. D- and L-galacto (I, Beta-C-Lyxose)
2. D- and L-altro (II, - ent II, Alpha-C-Lyxose, Alpha-C-Ribose)
3. D- and L-allo (VI, Beta-C-Ribose)
4. Unselective lyxose and ribose C-glycosides

Part B: Introduction on C-Glycosides of Arabinose Xylose
5. D- and L-gluco (III, ent-III, Beta-Arabinose, Beta-Xylose)
6. D- and L-idose (V, ent-V, Alpha-D-Xylose, Alpha-L-Xylose)
7. D- and L-manno (VII, ent-VII, Alpha-C-Arabinose)
8. Unselective arabinose and xylose C-glycosides

Details

No. of pages:
794
Language:
English
Copyright:
© Academic Press 2018
Published:
Imprint:
Academic Press
Paperback ISBN:
9780128037393

About the Author

Peter Goekjian

Dr. Peter Goekjian has been Professor of Chemistry at Université Claude Bernard–Lyon 1, France, since September 2000. His research interests are carbohydrate chemistry, total synthesis of glycosidic natural products, targeted methodology, and the role of glycosylation in signal transduction and gene expression. He was involved in the early work on the use of C-glycosides as conformational probes in the late 1980s and early 1990s.

Affiliations and Expertise

Chemistry Department, Claude Bernard University Lyon 1, Lyon, France

Arnaud Haudrechy

Dr. Arnaud Haudrechy has been a Professor of Chemistry at the Université of Reims Champagne Ardenne, France, since September 2003. His research interests include carbohydrate chemistry, total synthesis of natural substances, development of methodologies, and didactical techniques. He was involved in the early work on the use of C-glycosides as conformational probes in the late 1980s and early 1990s.

Affiliations and Expertise

Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France

Boudjema Menhour

Dr. Boudjema Menhour has a PhD in Organic Chemistry and is a researcher at the Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France. He research interests include developing a synthesis of carbohydrate analogues, targeting a specific activity, such as immunostimulatory, and eliciting properties.

Affiliations and Expertise

Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France

Claire Coiffier

Claire Coiffier, PhD, is a researcher at the Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France. She has worked on the top-down approach for the synthesis of biologically active substrates and on the analysis of preferred conformations of C-furanosides, using theoretical chemistry.

Affiliations and Expertise

Institute of Molecular Chemistry, Reims (ICMR), University of Reims Champagne-Ardenne, Reims, France