Facile and regioselective preparation of partly O-benzylated d-glucopyranose acetates via acid-mediated simultaneous debenzylation–acetolysis

Fully O-benzylated methyl α-d-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride. Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, and 2-O-benzyl-d-glucopyranose acetates were facilitated in greater than 80% yields. The key points of the preparative reactions were the control of the acid strength and choice of suitable substrates.

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