Issue 10, 2013
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Chemical Society Reviews

Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics†

Eric Leclerc,*ab   Xavier Pannecoucke,a   Mélanie Ethève-Quelquejeuc  and  Matthieu Sollogoub*c  

* Corresponding authors

a UMR6014 & FR3038–CNRS, Université et INSA de Rouen, 1 rue Tesnière, 76821 Mont Saint-Aignan Cedex, France

b Institut Charles Gerhardt UMR 5253 CNRS-UM2-UM1-ENSCM 8, rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France
E-mail: eric.leclerc@enscm.fr

c UPMC Université Paris 06, Sorbonne Université, Institut Universitaire de France, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), FR 2769, C. 181, 4 place Jussieu, 75005 Paris, France
E-mail: matthieu.sollogoub@upmc.fr

Abstract

Fluoro-C-glycosides and fluoro-carbasugars are a particular subclass of hydrolytically stable glycomimetics that are expected to have different, hopefully improved properties thanks to the stereoelectronic features of the fluoroalkyl moiety. This review summarizes the studies devoted to the synthesis of such structures as well as the studies regarding their conformational behaviour and their potential as carbohydrate analogues.

Graphical abstract: Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics

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Article information

DOI
https://doi.org/10.1039/C2CS35403A
Article type
Tutorial Review
Submitted
01 Oct 2012
First published
04 Dec 2012

Chem. Soc. Rev., 2013,42, 4270-4283

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Fluoro-C-glycosides and fluoro-carbasugars, hydrolytically stable and synthetically challenging glycomimetics

E. Leclerc, X. Pannecoucke, M. Ethève-Quelquejeu and M. Sollogoub, Chem. Soc. Rev., 2013, 42, 4270 DOI: 10.1039/C2CS35403A

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