Regiospecific enzymic acylation of butyl α-D-glucopyranoside

Article abstract of DOI:10.1016/0008-6215(93)87045-T

Acylated sugars are important sources of surfactants and pharmaceutical materials. Regioselective acylation is necessary for the synthesis of carbonhydrate derivatives where selective protection and deprotection of hydroxyl groups is critical. The authors report reaction conditions that lead to high yields of diesters in a regiospecific manner. The esters were obtained in high yield by enzymic reverse hydrolysis which involved the azeothropic removal of water from mixtures of the acid and substrate in hexane. The use of an apolar solvent such as hexane limits acyl-group migration. The purity of the products was determined by GLC after silylation and characterized on the basis of ¹³C NMR data.