(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-3-triethylsilanyloxy-cyclopentyl]-hept-6-enoic acid methyl ester | 879880-58-7

• 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: (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-3-triethylsilanyloxy-cyclopentyl]-hept-6-enoic acid methyl ester
• 英文别名: methyl (E,5S)-5-[tert-butyl(dimethyl)silyl]oxy-7-[(1R,2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-(2-oxoethyl)-3-triethylsilyloxycyclopentyl]hept-6-enoate
• CAS: 879880-58-7
• 化学式: C₃₃H₆₆O₆Si₃
• 分子量: 643.14
• InChiKey: CASGGWZYVZHTCJ-DLWCAKQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  42
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-3-triethylsilanyloxy-cyclopentyl]-hept-6-enoic acid methyl ester 在 盐酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 8.67h， 生成 (E)-(S)-7-[(1R,2S,3R,5S)-3,5-Dihydroxy-2-((2Z,5Z)-octa-2,5-dienyl)-cyclopentyl]-5-hydroxy-hept-6-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of 8,12-iso-iPF_3α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center

  摘要：

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.

  DOI：

  10.1021/jo051916x
• 作为产物：
  描述：

  methyl 5(S)-hydroxy-hept-6-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 102.58h， 生成 (E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-oxo-ethyl)-3-triethylsilanyloxy-cyclopentyl]-hept-6-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of 8,12-iso-iPF_3α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center

  摘要：

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.

  DOI：

  10.1021/jo051916x

文献信息

• Total Synthesis of 8,12-<i>iso</i>-iPF₃_α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center
  作者：Sheila H. Jacobo、Chih-Tsung Chang、Gue-Jae Lee、John A. Lawson、William S. Powell、Domenico Pratico、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1021/jo051916x

  日期：2006.2.1

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.