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L-FRUCTO- AND D-PSICOFURANOSYLATION REACTIONS CATALYZED BY SCANDIUM TRIFLATE

  作者 YAMANOI TAKASHI; ISHIYAMA TOSHIAKI; ODA YOSHIKI; MATSUDA SHO; WATANABE MIKIO  
  选自 期刊  Heterocycles;  卷期  2010年81-5;  页码  1141-1147  
  关联知识点  
 

[摘要]This paper describes the formation of L-fructo- and D-psicofuranosidic bonds by the scandium triflate catalyzed glycosidation. The reaction of the benzoylated L-fructofuranosyl acetate with an alcohol in the presence of 5 mol% scandium triflate in toluene at room temperature for 3 h stereoselectively afforded the corresponding alpha-L-fructofuranoside in good yields. Several alpha-D-psicofuranosides were predominantly obtained in good yields by the reactions between the benzoylated D-psicofuranosyl acetate and alcohols under similar reaction conditions. This method successfully provided the sucrose mimics composed of D-glucopyranose and L-fructofuranose or D-psicofuranose.

 
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