C-Furanosides: Synthesis and Stereochemistry

by Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour

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. Synthesis and Stereochemistry provides a much-needed overview of synthetic and stereochemical principles for C - 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, 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.

794 pages, Paperback

Published December 14, 2017