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

Academic Article
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publication date

  • 1999

abstract

  • [formula: see text] 2-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-10 and 22 are extremely useful precursors of 2-deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation reactions at -78 degrees C with a range of glycosyl acceptors using TBS-OTf as the activating agent. beta-Glycosides are obtained with > or = 19:1 selectivity in six of the seven examples reported herein.