Concerning the origin of the high beta-selectivity of glycosidation reactions of 2-deoxy-2-iodo-glucopyranosyl trichloroacetimidates.
[structure: see text] Studies on the glycosidation reactions of conformationally constrained glycosyl imidates 8a and 8b were performed to evaluate the possible involvement of "conformationally inverted" oxonium ion intermediates in glycosidation reactions with 2-deoxy-2-iodo-glucopyranosyl donors. The mechanistic implications of this study are discussed, and intermediates 23 and 24 are invoked to rationalize the observed beta-selectivities.
Chong
Pek Y
PY
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.
Roush
William R
WR
D002236:Carbohydrate Conformation; D062845:Chloroacetates; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D014238:Trichloroacetic Acid / Q000138:chemical synthesis* / Q000737:chemistry
D062845:Chloroacetates; D006027:Glycosides; D014238:Trichloroacetic Acid