Regioselective Benzoylation of 4,6-O-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

4836826

Reference Type

Journal Article

Title

Regioselective Benzoylation of 4,6-O-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals

Author(s)

Evtushenko, EV

Year

2015

Is Peer Reviewed?

Yes

Journal

Journal of Carbohydrate Chemistry
ISSN: 0732-8303

Volume

Issue

Page Numbers

41-54

DOI

10.1080/07328303.2014.996291

Web of Science Id

WOS:000349119200004

Abstract

Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)(2) as a promoter gave 2-benzoates for alpha-D-glucopyranosides and alpha-D-mannopyranosides and 3-benzoates for beta-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst in all studied cases led to regioselective 3-O-substitution.

Keywords

Regioselective benzoylation; Copper (II) trifluoroacetate; 4,6-O-benzylidene acetals; Molybdenum (VI) dioxide bis(acetylacetonate)