2-Deoxy-2-iodo- and 2-Deoxy-2-bromo-α-glucopyranosyl Trichloroacetimidates: Highly Reactive and Stereoselective Donors for the Synthesis of 2-Deoxy-β-glycosides
- 21 August 1999
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (6) , 891-893
- https://doi.org/10.1021/ol9908070
Abstract
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.Keywords
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