C-Furanosides
Synthesis and Stereochemistry
- 794 pages
- English
- ePUB (mobile friendly)
- Available on iOS & Android
C-Furanosides
Synthesis and Stereochemistry
About This Book
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.
- 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target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases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
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Table of contents
- Cover image
- Title page
- Table of Contents
- Copyright
- The Stereochemistry of C-Furanosides
- Part A. C-Glycosides of Lyxose and Ribose: galacto-, altro- and allo- Configurations
- Part B. C-Glycosides of Arabinose and Xylose: gluco-, ido- and manno- Configurations
- Part C. Applications of C-Furanosides
- Part D. 1H NMR Vicinal Coupling Constants of C-Furanosides
- Index