Details

Autor(en) / Beteiligte

• Chong, Pek Y
• Roush, William R

Titel

Concerning the Origin of the High β-Selectivity of Glycosidation Reactions of 2-Deoxy-2-iodo-glucopyranosyl Trichloroacetimidates

Ist Teil von

• Organic letters, 2002-12, Vol.4 (25), p.4523-4526

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2002

Quelle

MEDLINE

Beschreibungen/Notizen

• 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 β-selectivities.