(2E,4E,6E,8R,9R,10S,11R,12R,13S,14E)-11,13,17-trihydroxy-9-methoxy-8,10,12,14-tetramethylheptadeca-2,4,6,14-tetraenoic acid | 1187629-88-4

• 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: (2E,4E,6E,8R,9R,10S,11R,12R,13S,14E)-11,13,17-trihydroxy-9-methoxy-8,10,12,14-tetramethylheptadeca-2,4,6,14-tetraenoic acid
• CAS: 1187629-88-4
• 化学式: C₂₂H₃₆O₆
• 分子量: 396.524
• InChiKey: KFSANIRCOYIESP-GFGLWDEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2E,4E,6E,8R,9R,10R,11S,12R,13S,14E)-2-(trimethylsilyl)ethyl 17-(tert-butyldiphenylsilyloxy)-9-methoxy-8,10,12,14-tetramethyl-11,13-bis(triethylsilyloxy)heptadeca-2,4,6,14-tetraenoate 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.25h， 以53%的产率得到(2E,4E,6E,8R,9R,10S,11R,12R,13S,14E)-11,13,17-trihydroxy-9-methoxy-8,10,12,14-tetramethylheptadeca-2,4,6,14-tetraenoic acid
  参考文献：
  名称：

  Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide

  摘要：

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.

  DOI：

  10.1021/jo9012833

文献信息

• Relative Stereochemical Determination and Synthesis of the C1−C17 Fragment of a New Natural Polyketide
  作者：Etienne Fleury、Marie-Isabelle Lannou、Olivia Bistri、François Sautel、Georges Massiot、Ange Pancrazi、Janick Ardisson

  DOI：10.1021/jo9012833

  日期：2009.9.18

  The challenging determination of the relative stereochemistry of a complex natural polyketide portion was achieved. After careful NMR analysis, a concise synthesis of a set of possible relative diastereomers (only 6 diastereomers out of the 32 initially envisioned) has been carried out using a common strategy based on enantioselective aldol reactions. With a high predictability, final NMR comparison established the relative stereochemistry of the C1-C17 fragment of this natural product.