Reactions of difluoroenoxysilanes with glycosyl donors: synthesis of difluoro-C-glycosides and difluoro-C-disaccharides |
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Authors: | Berber H Brigaud T Lefebvre O Plantier-Royon R Portella C |
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Affiliation: | Laboratoire des Réactions Sélectives et Applications Associé au CNRS (UMR 6519), Université de Reims, Faculté des Sciences, Reims, France. |
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Abstract: | 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. |
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