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  • Regioselective benzoylation of glycopyranosides by benzoic anhydride in the presence of Cu(CF3COO)2.

Regioselective benzoylation of glycopyranosides by benzoic anhydride in the presence of Cu(CF3COO)2.

Carbohydrate research (2012-08-29)
Evgeny V Evtushenko
ABSTRACT

Benzoylation of methyl and benzyl glycopyranosides by benzoic anhydride in acetonitrile in the presence of copper(II) trifluoroacetate as a promoter has given monobenzoates with a good yield and high regioselectivity. The composition of monobenzoates depended both on a configuration of hydroxyl groups and on a configuration of aglycone. The simple syntheses of the monobenzoates of some glycosides are offered.

MATERIALS
Product Number
Brand
Product Description

Supelco
Trifluoroacetic acid, analytical standard
Sigma-Aldrich
Benzoic anhydride, ≥95%
Sigma-Aldrich
Trifluoroacetic acid, ReagentPlus®, 99%
Sigma-Aldrich
Trifluoroacetic acid, suitable for HPLC, ≥99.0%
Sigma-Aldrich
Trifluoroacetic acid, puriss. p.a., suitable for HPLC, ≥99.0% (GC)
Sigma-Aldrich
Trifluoroacetic acid, ≥99%, for protein sequencing