2-Deoxy-2-iodo- and 2-deoxy-2-bromo-alpha-glucopyranosyl trichloroacetimidates: highly reactive and stereoselective donors for the synthesis of 2-deoxy-beta-glycosides.

2-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8−10 and 22 are extremely useful precursors of 2-deoxy-β-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at −78 °C with a range of glycosyl acceptors using TBS-OTf as the activating agent. β-Glycosides are obtained with ≥ 19:1 selectivity in six of the seven examples reported herein.