PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE-TRANSFER-CATALYZED BENZOYLATION AND BENZYLATION

Partial substitution by phase transfer catalysis giving monobenzoylate d and monobenzylated products from 2,3- and from 4,6-diols in ethyl 1- thio-D-hexopyranosides with the beta-gluco-, beta-galacto- and alpha-m anno-configurations are described. Two disaccharide thioglucoside diol s with either the 2',3'-hydroxyl groups or the 4',6'-hydroxyl groups f ree were included in the study. Good yields of monosubstitution produc ts are obtained after chromatographic separations, making this a usefu l method for obtaining protected thioglycosides with a single hydroxyl group for further manipulations.