2-Deoxy-2-iodo-alpha-mannopyranosyl and -talopyranosyl acetates: highly stereoselective glycosyl donors for the synthesis of 2-deoxy-alpha-glycosides.
[formula: see text] TMS-OTf- or TBS-OTf-promoted glycosidation reactions of 2-deoxy-2-iodo-alpha-mannopyranosyl acetates 8-10 and the 2-deoxy-2-iodo-alpha-talopyranosyl acetate 11 provide the corresponding 2-deoxy-2-iodo-alpha-pyranosides, precursors to 2-deoxy-alpha-glycosides, as the only observed reaction products.
Roush
W R
WR
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
Narayan
S
S
D000085:Acetates / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D008358:Mannose / Q000737:chemistry*; D008969:Molecular Sequence Data; D013237:Stereoisomerism
D000085:Acetates; D006027:Glycosides; D008358:Mannose