title: Organosilicon-mediated regioselective acetylation of carbohydrates.
abstract: Organosilicon-mediated, regioselective acetylation of vicinal- and 1,3-diols is presented. Methyl trimethoxysilane or dimethyl dimethoxysilane was first used to form cyclic 1,3,2-dioxasilolane or 1,3,2-dioxasilinane intermediates, and subsequent acetate-catalyzed monoacylation was efficiently performed by addition of acetic anhydride or acetyl chloride under mild conditions. The reaction exhibited high regioselectivity, resulting in the same protection pattern as in organotin-mediated schemes.
authors.affiliation: Huazhong University of Science & Technology, School of Chemistry & Chemical Engineering, Luoyu Road 1037, 430074 Hongshan, Wuhan, PR China.
authors.forename: Yixuan
authors.initials: Y
authors.lastname: Zhou
authors.forename: Olof
authors.initials: O
authors.lastname: Ramström
authors.forename: Hai
authors.initials: H
authors.lastname: Dong
mesh_terms: D000107:Acetylation; D002241:Carbohydrates / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D009947:Organotin Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D017646:Organosilicon Compounds; D009947:Organotin Compounds