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Protection of Hydroxy Groups with Diphenylmethyl and 9‐Fluorenyl Trichloroacetimidates − Effect on Anomeric Stereocontrol
Author(s) -
Ali Ibrahim A. I.,
Ashry El Sayed H. El,
Schmidt Richard R.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300323
Subject(s) - chemistry , anomer , stereochemistry , glycosylation , combinatorial chemistry , medicinal chemistry , biochemistry
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)