C-Furanosides: Synthesis and Stereochemistry

2017 | Science & Mathematics

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.

Peter Goekjian (Author)

Arnaud Haudrechy (Author)

Boudjema Menhour (Author)

Claire Coiffier (Author)