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 pK(a) of the acid on the stereoselectivity of the reaction

Article abstract of DOI:10.1016/S0008-6215(00)90559-7

Glycosides (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- an