title: Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis.
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.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
authors.forename: Yang
authors.initials: Y
authors.lastname: Cao
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Okada
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Yamada
mesh_terms: D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D000089:Acetic Anhydrides / Q000737:chemistry; D000143:Acids / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D000089:Acetic Anhydrides; D000143:Acids; D001593:Benzyl Compounds; D006027:Glycosides