(R)-1-((4S,5R)-2,2-dimethyl-5-((Z)-tridec-1-en-1-yl)-1,3-dioxolan-4-yl)ethane-1,2-diol | 1369558-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-((4S,5R)-2,2-dimethyl-5-((Z)-tridec-1-en-1-yl)-1,3-dioxolan-4-yl)ethane-1,2-diol
• CAS: 1369558-59-7
• 化学式: C₂₀H₃₈O₄
• 分子量: 342.519
• InChiKey: MXWYURKAYSOAEZ-VMBHCNEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  24.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((4S,5R)-2,2-dimethyl-5-((Z)-tridec-1-en-1-yl)-1,3-dioxolan-4-yl)ethane-1,2-diol 在 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以100%的产率得到
  参考文献：
  名称：

  Asymmetric Synthesis of (-)-Muricatacin’s Analogue (4S,5R)-5-Hydroxy-4-octadecanolide Exhibiting the Cytotoxicity against Esphageal Cancer Cells

  摘要：

  An efficient and facile synthesis, in six steps and 50% overall yield from commercial D-(-)-lyxose as starting material via twice Wittig olefination and one-pot deisopropylidenation and intramolecular lactonization, of the enantiopure (4S,5R)-(+)-5-hydroxy-4-octadecanolide (2), analogue of (-)-muricatacin, and the cytotoxic activity against CE48T cell line (human esophageal carcinoma) are described and the biological activity is the first shown in the literature.

  DOI：

  10.3987/com-11-12397
• 作为产物：
  描述：

  2,3-O-isopropylidene-D-lyxofuranose 、 十二烷基三苯基溴化膦 在 双(三甲基硅烷基)氨基钾 作用下， 反应 7.0h， 以81%的产率得到(R)-1-((4S,5R)-2,2-dimethyl-5-((Z)-tridec-1-en-1-yl)-1,3-dioxolan-4-yl)ethane-1,2-diol
  参考文献：
  名称：

  Asymmetric Synthesis of (-)-Muricatacin’s Analogue (4S,5R)-5-Hydroxy-4-octadecanolide Exhibiting the Cytotoxicity against Esphageal Cancer Cells

  摘要：

  An efficient and facile synthesis, in six steps and 50% overall yield from commercial D-(-)-lyxose as starting material via twice Wittig olefination and one-pot deisopropylidenation and intramolecular lactonization, of the enantiopure (4S,5R)-(+)-5-hydroxy-4-octadecanolide (2), analogue of (-)-muricatacin, and the cytotoxic activity against CE48T cell line (human esophageal carcinoma) are described and the biological activity is the first shown in the literature.

  DOI：

  10.3987/com-11-12397