Reactions of difluoroenoxysilanes with glycosyl donors: synthesis of difluoro-C-glycosides and difluoro-C-disaccharides.
Difluoroenoxysilanes, prepared from acylsilanes and trifluoromethyltrimethylsilane under fluoride activation, were glycosylated with some glycosyl donors (acylglycosides, glycals) to yield difluoro-C-glycosides with a difluoromethylene group in the place of the anomeric oxygen. This reaction strongly depends on the substituent in the 2-position of the glycosyl donor. Application of this methodology to a xylose-derived acylsilane led to the formation of difluoro-C-disaccharides as an isosteric O-glycosyl mimetic.
Berber
H
H
Laboratoire des Réactions Sélectives et Applications Associé au CNRS (UMR 6519), Université de Reims, Faculté des Sciences, Reims, France.
Brigaud
T
T
Lefebvre
O
O
Plantier-Royon
R
R
Portella
C
C