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