Glycosylation of vicinal di- and trifluorinated glucose and galactose donors
Kler Huonnic1, Bruno Linclau1,2
1School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK.
Abstract:
The acid-catalysed formation of glycosidic bonds is more difficult when glycosyl donors are fluorinated, especially at the 2-position. Here we report high-yielding glycosidation and glycosylation reactions of 2,3-difluorinated- and 2,3,4-trifluorinated gluco- and galactopyranoside donors with a variety of acceptors under conventional trichloroacetimidate/TMSOTf activation in moderate to high anomeric selectivities. This methodology allows access to highly fluorinated glycans, illustrated with the synthesis of a pentafluorinated disaccharide.
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