gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose

João Sardinha; Samuel Guieu; Aurélie Deleuze; M Carmen Fernández-Alonso; Amelia Pilar Rauter; Pierre Sinaÿ; Jérôme Marrot; Jesús Jiménez-Barbero; Matthieu Sollogoub

doi:10.1016/j.carres.2007.05.021

gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose

Carbohydr Res. 2007 Sep 3;342(12-13):1689-703. doi: 10.1016/j.carres.2007.05.021. Epub 2007 May 23.

Authors

João Sardinha¹, Samuel Guieu, Aurélie Deleuze, M Carmen Fernández-Alonso, Amelia Pilar Rauter, Pierre Sinaÿ, Jérôme Marrot, Jesús Jiménez-Barbero, Matthieu Sollogoub

Affiliation

¹ Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France.

PMID: 17559817
DOI: 10.1016/j.carres.2007.05.021

Abstract

5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesized from D-mannose and D-galactose, using a rearrangement strategy.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrate Conformation
Fluorine / chemistry*
Galactose / analogs & derivatives
Galactose / chemistry*
Indicators and Reagents
Mannose / analogs & derivatives
Mannose / chemistry*
Models, Molecular

Substances

Indicators and Reagents
Fluorine
Mannose
Galactose