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C-Furanosides: Synthesis and Stereochemistry

Abstract : 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.
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https://hal.univ-reims.fr/hal-03623469
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Submitted on : Tuesday, March 29, 2022 - 5:02:35 PM
Last modification on : Saturday, September 24, 2022 - 12:10:06 PM

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Peter Goekjian, Arnaud Haudrechy, Boudjema Menhour, Coiffier Claire. C-Furanosides: Synthesis and Stereochemistry. Elsevier, 2017, 978-0-12-803739-3. ⟨10.1016/C2015-0-00340-9⟩. ⟨hal-03623469⟩

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