Silver(I) tetrafluoroborate as a potent promoter for chemical glycosylation.

We have identified silver tetrafluoroborate (AgBF(4)) as an excellent promoter for the activation of various glycosyl donors including glycosyl halides, trichloroacetimidates, thioimidates, etc. Easy handling and no requirement for azeotropic dehydration prior to application makes AgBF(4) especially beneficial in comparison to the commonly used AgOTf. Selective activation of glycosyl halides or thioimidates over thioglycosides or n-pentenyl glycosides, including simple sequential one-pot syntheses, has been also demonstrated. Versatility of glycosyl thioimidates was further explored by converting these intermediates into a variety of other classes of glycosyl donors.