The conversion of 3-C-beta-D-galactopyranosyl phloroacetophenone to a spiroketal derivative.
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.
Kumazawa
T
T
Department of Materials Science and Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan. tk111@dip.yz.yamagata-u.ac.jp
Chiba
M
M
Matsuba
S
S
Sato
S
S
Onodera
J
J
D000098:Acetophenones / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis*
D000098:Acetophenones; D013141:Spiro Compounds; D005690:Galactose