2-(trimethylsilyl)ethyl (S,2Z,6E,8Z)-12-((2R,4S,6R)-4-hydroxy-6-methoxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,10-dimethyldodeca-2,6,8-trienoate | 127733-33-9

• 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: 2-(trimethylsilyl)ethyl (S,2Z,6E,8Z)-12-((2R,4S,6R)-4-hydroxy-6-methoxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,10-dimethyldodeca-2,6,8-trienoate
• CAS: 127733-33-9
• 化学式: C₂₈H₄₇NO₆SSi
• 分子量: 553.836
• InChiKey: MLYNCRGZKKOWAT-GGWZPKFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  94.09
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (S,2Z,6E,8Z)-12-((2R,4S,6R)-4-hydroxy-6-methoxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,10-dimethyldodeca-2,6,8-trienoate 在 四丁基氟化铵 作用下， 以 二甲基亚砜 为溶剂， 以71%的产率得到(2Z,6E,8Z)-(S)-12-[(2R,4S,6R)-4-Hydroxy-6-methoxy-6-((R)-2-oxo-thiazolidin-4-yl)-tetrahydro-pyran-2-yl]-3,10-dimethyl-dodeca-2,6,8-trienoic acid
  参考文献：
  名称：

  White, James D.; Kawasaki, Motoji, Journal of the American Chemical Society, 1990, vol. 112, # 12, p. 4991 - 4993

  摘要：

  DOI：
• 作为产物：
  描述：

  (2Z,6E,8Z,10S,13R)-2-(trimethylsilyl)ethyl 15-hydroxy-3,10-dimethyl-17-oxo-17-((R)-2-oxothiazolidin-4-yl)-13-((2-(trimethylsilyl)ethoxy)methoxy)heptadeca-2,6,8-trienoate 在 camphor-10-sulfonic acid 、 氢氟酸 作用下， 以 乙腈 为溶剂， 生成 2-(trimethylsilyl)ethyl (S,2Z,6E,8Z)-12-((2R,4S,6R)-4-hydroxy-6-methoxy-6-((R)-2-oxothiazolidin-4-yl)tetrahydro-2H-pyran-2-yl)-3,10-dimethyldodeca-2,6,8-trienoate
  参考文献：
  名称：

  White, James D.; Kawasaki, Motoji, Journal of the American Chemical Society, 1990, vol. 112, # 12, p. 4991 - 4993

  摘要：

  DOI：

文献信息

• Total synthesis of (+)-latrunculin A, an ichthyotoxic metabolite of the sponge Latrunculia magnifica and its C-15 epimer
  作者：James D. White、Motoji Kawasaki

  DOI：10.1021/jo00046a008

  日期：1992.9

  Latrunculin A (1), an ichthyotoxic metabolite of the sponge Latrunculia magnifica with potent inhibitory action on microfilament-mediated processes involved in cell division, was synthesized via a convergent approach. Construction of a major segment of the latrunculin backbone was accomplished by means of a three-component coupling of aldehyde 24, beta-keto ester 27, and phosphonium salt 26, which established the conjugated EZ-diene moiety of 31. The thiazolidinone subunit of 1 was elaborated in the form of 39 from L-cysteine and was linked to 35 without nitrogen protection. Final lactonization of 47 was carried out using the Mitsunobu protocol. A parallel sequence employing the epimeric seco acid 48 produced 15-epilatrunculin A.