[(2S,3S,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate | 1232836-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3S,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 1232836-52-0
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: ZYJUUZKDMZKDIS-UDIRLXJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate 、 乙酸酐 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1,3,4,6-tetra-O-benzoyl-β-L-fructofuranosyl acetate 、 1,3,4,6-tetra-O-benzoyl-α-L-fructofuranosyl acetate
  参考文献：
  名称：

  L-Fructo- and D-Psicofuranosylation Reactions Catalyzed by Scandium Triflate

  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.

  DOI：

  10.3987/com-10-11916
• 作为产物：
  描述：

  L-果糖 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到[(2S,3S,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  L-Fructo- and D-Psicofuranosylation Reactions Catalyzed by Scandium Triflate

  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.

  DOI：

  10.3987/com-10-11916