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Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-d-glucopyranoside, derivatives displaying a range of anomeric substituents

✍ Scribed by Jonathan J. Gridley; Helen M.I. Osborn; William G. Suthers

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 222 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01420-3

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✦ Synopsis

Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-l~-Dglucopyranoside, phenyl 4,6-O-benzylidene-I~-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-[~-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate.

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