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

Article abstract of DOI:10.1016/j.tetlet.2007.12.105

We have identified silver tetrafluoroborate (AgBF₄) as an excellent promoter for the activation of various glycosyl donors including glycosyl halides, trichloroacetimidates, and thioimidates. Easy handling and no requirement for azeotropic dehydration prior to application makes AgBF₄ 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 also been demonstrated. Versatility of glycosyl thioimidates was further explored by converting these intermediates into a variety of other classes of glycosyl donors.