Cover for C-Furanosides

C-Furanosides

Synthesis and Stereochemistry

Book2018

Authors:

Peter Goekjian, Arnaud Haudrechy, ... Claire Coiffier

C-Furanosides

Synthesis and Stereochemistry

Book2018

 

Cover for C-Furanosides

Authors:

Peter Goekjian, Arnaud Haudrechy, ... Claire Coiffier

About the book

Browse this book

Book description

Carbon analogs of carbohydrates, dubbed C-glycosides, have remained an important and interesting class of mimetics, be it in natural product synthesis, for pharmacological applicat ... read full description

Browse content

Table of contents

Actions for selected chapters

Select all / Deselect all

  1. Full text access
  2. Book chapterNo access

    Index

    Pages 747-771

About the book

Description

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

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. 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, C-Furanosides: Synthesis and Stereochemistry enables the reader to determine the best approach to a particular C-glycoside compound, and also hopes to provide a certain level of rationalization and predictability for the synthesis of new systems.

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

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. 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, C-Furanosides: Synthesis and Stereochemistry enables the reader to determine the best approach to a particular C-glycoside compound, and also hopes to provide a certain level of rationalization and predictability for the synthesis of new systems.

Key Features

  • Provides a comprehensive review of the growing literature in C-furanosides
  • Enables readers to choose the most convenient approach to access a defined target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases
  • Explores the various rational models for stereochemical analysis of furanoside reactivity, with a clear distinction made between physical chemical mechanisms and stereochemical models
  • Provides a comprehensive review of the growing literature in C-furanosides
  • Enables readers to choose the most convenient approach to access a defined target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases
  • Explores the various rational models for stereochemical analysis of furanoside reactivity, with a clear distinction made between physical chemical mechanisms and stereochemical models

Details

ISBN

978-0-12-803739-3

Language

English

Published

2018

Copyright

Copyright © 2018 Elsevier Inc. All rights reserved.

Imprint

Academic Press

Authors

Peter Goekjian

Arnaud Haudrechy

Boudjema Menhour

Claire Coiffier