Application of ortho esterification under kinetically controlled conditions to the selective acylation in the D-gluco-, D-ribo- and D-xylo-furanose series

Article abstract of DOI:10.1055/s-1995-3955

The ortho esterification of various glucofuranoses in the D-ribo, D-xylo and D-gluco series under kinetic control was obtained through the action of 1,1-dimethoxyethene (a ketene acetal) on the monosaccharide using mild acid conditions. The selective hydrolysis of the methoxyethylidene derivatives thus obtained, gave access to α-hydroxy acetates which are useful synthetic intermediates.