C-Furanosides
Synthesis and Stereochemistry
Nonfiction, Science & Nature, Science, Chemistry, Organic, General Chemistry
| Author: | Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier | ISBN: | 9780128037898 |
| Publisher: | Elsevier Science | Publication: | November 30, 2017 |
| Imprint: | Academic Press | Language: | English |
| Author: | Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Claire Coiffier |
| ISBN: | 9780128037898 |
| Publisher: | Elsevier Science |
| Publication: | November 30, 2017 |
| Imprint: | Academic Press |
| Language: | English |
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target in natural products synthesis or pharmacology and make reasonable predictions for the stereochemical outcome in unpublished cases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
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
