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

Ali Ibrahim A. I. | Zendy; Ashry El Sayed H. El | Zendy; Schmidt Richard R. | Zendy

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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)

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