tert-butyl (2R,3R)-2-chloro-3-dodecanoyloxytetradecanoate | 163562-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (2R,3R)-2-chloro-3-dodecanoyloxytetradecanoate
• CAS: 163562-87-6
• 化学式: C₃₀H₅₇ClO₄
• 分子量: 517.233
• InChiKey: OVRGCLMMKAHODB-IXCJQBJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  35
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3R)-2-chloro-3-dodecanoyloxytetradecanoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.0h， 以97%的产率得到tert-butyl (R)-3-dodecanoyloxytetradecanoate
  参考文献：
  名称：

  On a practical synthesis of β-hydroxy fatty acid derivatives

  摘要：

  An efficient synthesis of three homochiral beta-hydroxy fatty acid derivatives, which have been utilized in our total synthesis of lipid A, is reported. The synthesis features Sharpless asymmetric dihydroxylation of an unsaturated ester, regioselective conversion of a diol into acyloxy chlorides, and a reductive removal of the chloro group.

  DOI：

  10.1016/0957-4166(95)00106-y
• 作为产物：
  描述：

  十二腈 在 三甲基氯硅烷 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 tert-butyl (2R,3R)-2-chloro-3-dodecanoyloxytetradecanoate
  参考文献：
  名称：

  On a practical synthesis of β-hydroxy fatty acid derivatives

  摘要：

  An efficient synthesis of three homochiral beta-hydroxy fatty acid derivatives, which have been utilized in our total synthesis of lipid A, is reported. The synthesis features Sharpless asymmetric dihydroxylation of an unsaturated ester, regioselective conversion of a diol into acyloxy chlorides, and a reductive removal of the chloro group.

  DOI：

  10.1016/0957-4166(95)00106-y

文献信息

• On a practical synthesis of β-hydroxy fatty acid derivatives
  作者：Masato Oikawa、Shoichi Kusumoto

  DOI：10.1016/0957-4166(95)00106-y

  日期：1995.4

  An efficient synthesis of three homochiral beta-hydroxy fatty acid derivatives, which have been utilized in our total synthesis of lipid A, is reported. The synthesis features Sharpless asymmetric dihydroxylation of an unsaturated ester, regioselective conversion of a diol into acyloxy chlorides, and a reductive removal of the chloro group.