Synthesis of C-pentopyranosylphloroacetophenone derivatives and their anomerization.
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.
Kumazawa
T
T
Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, Japan. tk111@dip.yz.yamagata-u.ac.jp
Saito
T
T
Matsuba
S
S
Sato
S
S
Onodera
J
J
D000098:Acetophenones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010429:Pentoses / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000098:Acetophenones; D010429:Pentoses