Synthesis of aryl d-gluco- and d-galacto-pyranosides and 1-O-acyl-d-gluco- and -d-gluco-pyranoses exploiting the mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction

Abstract

Glycosids (α- and β-d-glucosides and -d-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-d-gluco- and -d-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the β-d anomer increases with the pKa of the acid component. © 1992.