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Synthesis of C-pentopyranosylphloroacetophenone derivatives and their anomerization
T Kumazawa1, T Saito, S Matsuba
1Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, Japan. tk111@dip.yz.yamagata-u.ac.jp
Abstract:
A 3-C-beta-D-xylopyranosylphloroacetophenone derivative was synthesized via reaction of 2,3,4-tri-O-benzyl-alpha-D-xylopyranosyl fluoride and 2,4-di-O-benzylphloroacetophenone in the presence of boron trifluoride diethyl etherate. Alternatively, the reaction of 2,3,4-tri-O-benzyl-beta-L-arabinopyranosyl fluoride with 2,4-di-O-benzylphloroacetophenone afforded both the 3-C-alpha-L- and the 3-C-beta-L-arabinopyranosylphloroacetophenone derivatives under identical reaction conditions. The C-beta-L-arabinoside, the thermodynanic product, was produced via anomerization of the C-alpha-L-arabinoside, the kinetic product during the reaction. The composition of this product mixture is apparently dictated by both 1,3-diaxial and 2,4-diaxial interactions.