The Regioselective Acylation of Sugars Derivatives

Intensive research has been done on the selective protection and deprotection of the hydroxyl group of carbohydrates (44-48). In general, chemical preparation of protected sugars with free primary hydroxyl groups may require several steps such as tritylation, esterification, and acid-catalyzed detritilation. Using enzyme-catalyzed selective acylation or deacylation, one or two steps may complete the synthesis. Some proteases possess both esterase and protease activities. Alcalase has both activities, with preferred esterase activity resulting in ester formation from a primary alcohol. The following procedure describes the alcalase-catalyzed regioselective acylation of (ethyl 2-acetamido-2-deoxy-1-thio-D-glucose) at the C-6 hydroxyl position using vinyl benzoate in 2-methyl-2-pro-panol as an irreversible acylation agent. The reaction is shown in Fig. 3.

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