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.
[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.
Roush
W R
WR
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
Gung
B W
BW
Bennett
C E
CE
D000081:Acetamides; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D062845:Chloroacetates; D006027:Glycosides; D014238:Trichloroacetic Acid; C009528:trichloroacetamide