Regioselective acylation of methyl α-D-glucopyranoside and methyl α-D-mannopyranoside by means of bis(2-oxooxazolidin-3-yl)phosphinic chloride (BOP-Cl)

Abstract

A new synthetic procedure is presented which allows the regioselective acylation of methyl α-D-glucopyranoside and methyl α-D-mannopyranoside at the primary hydroxy group by means of bis(2-oxooxazolidin-3-yl)phosphinic chloride (BOP-Cl) and aromatic or aliphatic carboxylic acids. 2.6-O- and 3,6-O-diacylated derivatives have been obtained as side-products from gluco- and manno-pyranosides, respectively. Both yields and regioselectivity are comparable to those obtained in the lipase-catalysed derivatizations.