REGIOSELECTIVE ACYLATION OF METHYL ALPHA-D-GLUCOPYRANOSIDE AND METHYLALPHA-D-MANNOPYRANOSIDE BY MEANS OF BIS(2-OXOOXAZOLIDIN-3-YL)PHOSPHINIC CHLORIDE (BOP-CL)

Authors
LIGUORI A PROCOPIO A ROMEO G SINDONA G UCCELLA N
Citation
A. Liguori et al., REGIOSELECTIVE ACYLATION OF METHYL ALPHA-D-GLUCOPYRANOSIDE AND METHYLALPHA-D-MANNOPYRANOSIDE BY MEANS OF BIS(2-OXOOXAZOLIDIN-3-YL)PHOSPHINIC CHLORIDE (BOP-CL), Journal of the Chemical Society. Perkin transactions. I, (15), 1993, pp. 1783-1786
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
15
Year of publication
1993
Pages
1783 - 1786
Database
ISI
SICI code
0300-922X(1993):15<1783:RAOMAA>2.0.ZU;2-X
Abstract
A new synthetic procedure is presented which allows the regioselective acylation of methyl alpha-D-glucopyranoside and methyl alpha-D-mannop yranoside at the primary hydroxy group by means of bis(2-oxooxazolidin -3-yl)phosphinic chloride (BOP-Cl) and aromatic or aliphatic carboxyli c acids. 2,6-O- and 3,6-O-diacylated derivatives have been obtained as side-products from gluco- and manno-pyranosides, respectively. Both y ields and regioselectivity are comparable to those obtained in the lip ase-catalysed derivatizations.