title: Organotin-catalyzed highly regioselective thiocarbonylation of nonprotected carbohydrates and synthesis of deoxy carbohydrates in a minimum number of steps.
abstract: Nonprotected carbohydrates: The catalytic regioselective thiocarbonylation of carbohydrates by using organotin dichloride under mild conditions was demonstrated. The reaction afforded various deoxy saccharides in high yields and excellent regioselectivity in a minimum number of steps. The regioselectivity of the thiocarbonylation is attributed to the intrinsic character of the carbohydrates based on the stereorelationship of their hydroxy groups (see scheme).
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan. muramatu@nagasaki-u.ac.jp
authors.forename: Wataru
authors.initials: W
authors.lastname: Muramatsu
authors.forename: Satoko
authors.initials: S
authors.lastname: Tanigawa
authors.forename: Yuki
authors.initials: Y
authors.lastname: Takemoto
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Yoshimatsu
authors.forename: Osamu
authors.initials: O
authors.lastname: Onomura
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D009947:Organotin Compounds