Reactions of carbohydrate α-keto toluene-p-sulphonates. Reaction of methyl 4,6-O-benzylidene-2-O-toluene-p-sulphonyl-α-D-ribo-hexopyranosid-3-ulose with triethylamine–methanol

Abstract

Reaction of methyl 4,6-O-benzylidene-2-O-toluene-p-sulphonyl-α-D-ribo-hexopyranosid-3-ulose (I) with triethylamine–methanol yields methyl 2,3-anhydro-4,6-O-benzylidene-3-methoxy-α-D-allopyranoside (II), methyl 4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose dimethyl acetal (III; RH), and a derivative of 3-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (IV).