The conversion of 3-C-beta-D-galactopyranosyl phloroacetophenone to a spiroketal derivative |
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| Authors: | Kumazawa T Chiba M Matsuba S Sato S Onodera J |
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| Institution: | Department of Materials Science and Engineering, Faculty of Engineering, Yamagata University, Yonezawa, Japan. tk111@dip.yz.yamagata-u.ac.jp |
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| 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. |
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