Protection of Hydroxy Groups with Diphenylmethyl and 9‐Fluorenyl Trichloroacetimidates − Effect on Anomeric Stereocontrol

Abstract The use of O ‐diphenylmethyl (DPM) and the O ‐(9‐fluorenyl) (Fl) trichloroacetimidates permitted efficient protection of alcohols. The compatibility of these groups with other chemical manipulations is demonstrated. Glucosylation of typical acceptors with an O ‐glucopyranosyl trichloroacetimidate as donor having a DPM group at 2‐O afforded β‐glucopyranosides, thus demonstrating anchimeric assistance of the DPM group in the anomeric stereocontrol. This effect was also observed in mannopyranoside synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)