title: The conversion of 3-C-beta-D-galactopyranosyl phloroacetophenone to a spiroketal derivative.
abstract: Treatment of 3-C-beta-D-galactopyranosylphloroacetophenone in hot water with a catalytic amount of p-toluenesulfonic acid afforded a spiroketal compound as the main product. The chirality of the spiro carbon of the product was R, which is the opposite of the spiroketal obtained by the conversion of 3-C-beta-D-glucopyranosyl phloroacetophenone under identical conditions. The structure was determined by 1H-1H COSY, 1H-13C COSY, NOESY and HMBC spectroscopy.
authors.affiliation: Department of Materials Science and Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan. tk111@dip.yz.yamagata-u.ac.jp
authors.forename: T
authors.initials: T
authors.lastname: Kumazawa
authors.forename: M
authors.initials: M
authors.lastname: Chiba
authors.forename: S
authors.initials: S
authors.lastname: Matsuba
authors.forename: S
authors.initials: S
authors.lastname: Sato
authors.forename: J
authors.initials: J
authors.lastname: Onodera
mesh_terms: D000098:Acetophenones / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D000098:Acetophenones; D013141:Spiro Compounds; D005690:Galactose