Regiospecific synthesis of new methyl sulfoglucopyranoside-based surfactants: Nucleophilic displacement of a cyclic sulfate

A two-step regiospecific synthesis of a new class of anionic and amphoteric methyl α-D-glucopyranoside-based surfactants is described. Reaction of methyl α-D-glucopyranoside with thionyl chloride followed by oxidation of the resulting sulfite afforded the corresponding methyl α-D- glucopyranoside 4,6-cyclic sulfate in high yield. Nucleophilic displacement of this cyclic sulfate by different fatty acids and amines led to the corresponding methyl 6-O-acyl- or 6-amino-6-deoxy-4-sulfoglucopyranosides in very good yields. These newly synthesized sulfoglucopyranoside-based surfactants displayed low critical micelle concentration (CMC) values.