ethyl (24Z)-3β-hydroxycholesta-5,24-dien-26-oate | 1452773-07-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ethyl (24Z)-3β-hydroxycholesta-5,24-dien-26-oate
• CAS: 1452773-07-7
• 化学式: C₂₉H₄₆O₃
• 分子量: 442.682
• InChiKey: DNSANGNVKNRYKQ-NPVRXLIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (24Z)-3β-hydroxycholesta-5,24-dien-26-oate 在 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.25h， 以98%的产率得到(24Z)-26-hydroxydesmosterol
  参考文献：
  名称：

  Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

  摘要：

  Using 3 beta-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.015
• 作为产物：
  描述：

  3β-(ter-butyldimethylsilyloxy)chol-5-en-24-al 在 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 ethyl (24Z)-3β-hydroxycholesta-5,24-dien-26-oate
  参考文献：
  名称：

  Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

  摘要：

  Using 3 beta-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.015