(7E,11Z)-(5S,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid ethyl ester | 197068-67-0

• 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: (7E,11Z)-(5S,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid ethyl ester
• 英文别名: ethyl (5S,6S,7E,11Z)-5-acetyl-9-[tert-butyl(dimethyl)silyl]oxy-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]heptadeca-7,11-dienoate
• CAS: 197068-67-0
• 化学式: C₃₂H₅₈O₆Si
• 分子量: 566.894
• InChiKey: KYGKLLYCSZYMGY-AZSRVPNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  39
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (7E,11Z)-(5S,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid ethyl ester 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 生成 (7E,11Z)-(5S,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid 、 (7E,11Z)-(5R,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid
  参考文献：
  名称：

  Total Synthesis of Iso[4]-levuglandin E₂

  摘要：

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.

  DOI：

  10.1021/jo970858f
• 作为产物：
  描述：

  4-碘-丁酸乙酯 在 sodium hydride 、 (lithium)2(CN)(methyl)2cuprate 作用下， 以 四氢呋喃 为溶剂， 反应 252.83h， 生成 (7E,11Z)-(5S,6S)-5-Acetyl-9-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-heptadeca-7,11-dienoic acid ethyl ester
  参考文献：
  名称：

  Total Synthesis of Iso[4]-levuglandin E₂

  摘要：

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.

  DOI：

  10.1021/jo970858f

文献信息

• Total Synthesis of Iso[4]-levuglandin E₂
  作者：Ganesamoorthy Subbanagounder、Robert G. Salomon、Krishna K. Murthi、Cynthia Brame、L. Jackson Roberts

  DOI：10.1021/jo970858f

  日期：1997.10.1

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.