Carbohydrate Research 1992-04-10

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

A Lubineau, E Meyer, P Place

Index: Carbohydr. Res. 228(1) , 191-203, (1992)

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Abstract

Glycosides (alpha- and beta-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 beta-D anomer increases with the pKa of the acid component.