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-CI) 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.
Regioselective acylation of methyl α-D-glucopyranoside and methyl α-D-mannopyranoside by means of bis(2-oxooxazolidin-3-yl)phosphinic chloride (BOP-CI)
Procopio A.;Sindona G.
;
1993-01-01
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-CI) 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.File in questo prodotto:
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