methyl (4R)-4-[(2S)-2-(hydroxymethyl)oxiran-2-yl]pentanoate | 139608-79-0

• 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: methyl (4R)-4-[(2S)-2-(hydroxymethyl)oxiran-2-yl]pentanoate
• CAS: 139608-79-0
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: QLUOIEUEEVCBBE-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (4R,5S)-5-(Hydroxymethyl)-4-methyl-5-<<(3,5-dinitrobenzoyl)oxy>methyl>-5-pentanolide 在 咪唑 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 methyl (4R)-4-[(2S)-2-(hydroxymethyl)oxiran-2-yl]pentanoate
  参考文献：
  名称：

  Stereoselective synthesis of the pyrrolizidine alkaloids (-)-integerrimine and (+)-usaramine

  摘要：

  Two routes to the pyrrolizidine alkaloid (-)-integerrimine (1) are described. The first, starting from methyl (R)-(-)-3-hydroxy-2-methylpropionate, proceeded in 19 steps to integerrinecic acid lactone (5) which was transformed to the necic acid derivative 30. The latter was coupled to protected retronecine 31, and the synthesis of 1 was completed by lactonization employing Vedejs' protocol. A second, shorter synthesis of (-)-1 was accomplished via 5, starting from (R)-(+)-beta-citronellol (36). This pathway invoked Katsuki-Sharpless epoxidation of 42 for stereoselective construction of the tertiary alcohol of integerrinecic acid. A parallel sequence proceeding via the stereoisomeric epoxide 44 led to the necic acid segment 75 of the alkaloid (+)-usaramine (2). This acid was coupled to the retronecine borane 82 and then lactonized to 2.

  DOI：

  10.1021/jo00034a017