Regiospecific Synthesis of New Methyl Sulfoglucopyranoside-Based Surfactants: Nucleophilic Displacement of a Cyclic Sulfate

摘要

A two-step regiospecific synthesis of a new class of anionic and amphoteric methyl #alpha#-D-glucopyranoside-based surfactants is described. Reaction of methyl #alpha#-D-glucopyranoside with thionyl chloride followed by oxidation of the resulting sulfite afforded the corresponding methyl #alpha#-D-glucopyranoside 4,6-cyclicsulfate 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.