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  • Title: Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis.
    Author: Cao Y, Okada Y, Yamada H.
    Journal: Carbohydr Res; 2006 Sep 25; 341(13):2219-23. PubMed ID: 16806130.
    Abstract:
    Fully O-benzylated methyl alpha-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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