C-furanosides: synthesis and stereochemistry

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

• 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target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases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 an interpretation of the outcome in terms of a reasonable number of stereochemical models