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

Authors
Roush, WR Gung, BW Bennett, CE
Citation
Wr. Roush et al., 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, ORG LETT, 1(6), 1999, pp. 891-893
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
6
Year of publication
1999
Pages
891 - 893
Database
ISI
SICI code
1523-7060(19990923)1:6<891:2A2T>2.0.ZU;2-T
Abstract
[GRAPHICS] 5-Deoxy-2-iodo- and 2-deoxy-2-bromoglucopyranosyl trichloroacetimidates 8-1 0 and 22 are extremely useful precursors of 2 deoxy-beta-glycosides. These reactive glycosyl donors undergo highly stereoselective glycosidation react ions at -78 degrees C with a range of glycosyl accepters using TBS-OTf as t he activating agent. beta-Glycosides are obtained with greater than or equa l to 19:1 selectivity in six of the seven examples reported herein.