title: Catalytic and regioselective oxidation of carbohydrates to synthesize keto-sugars under mild conditions.
abstract: A new catalytic and regioselective approach for the synthesis of keto-sugars is described. An organotin catalyst, Oc2SnCl2, in the presence of trimethylphenylammonium tribromide ([TMPhA](+)Br3(-)) accelerates the regioselective oxidation at the "axial"-OH group of 1,2-diol moieties in galactopyranosides. The reaction conditions can also be used for the regioselective oxidation of various carbohydrates.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University , 1-14 Bunkyo-machi, Nagasaki, Nagasaki 852-8521, Japan.
authors.forename: Wataru
authors.initials: W
authors.lastname: Muramatsu
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005697:Galactosides / Q000737:chemistry; D006601:Hexoses / Q000737:chemistry; D007661:Ketoses / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D002241:Carbohydrates; D005697:Galactosides; D006601:Hexoses; D007661:Ketoses; D009947:Organotin Compounds