7-{(1S,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester | 460045-03-8

• 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: 7-{(1S,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester
• 英文别名: methyl 7-[(1S,2R,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-hydroxycyclopentyl]heptanoate
• CAS: 460045-03-8
• 化学式: C₃₃H₆₆O₅Si₂
• 分子量: 599.055
• InChiKey: ARIFHBJXLQKNSF-LKWIVAFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.41
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-{(1S,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester 在 吡啶 、 lithium hydroxide 、 氢氟酸 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 8-iso PGF_1β
  参考文献：
  名称：

  Total synthesis of isoprostanes via the two-component coupling process

  摘要：

  A short total synthesis of isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. The F-1-isoprostanes were easily obtained by stereoselective reduction of the C-9 keto group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00898-5
• 作为产物：
  描述：

  7-{(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到7-{(1S,2R,3R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of isoprostanes via the two-component coupling process

  摘要：

  A short total synthesis of isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. The F-1-isoprostanes were easily obtained by stereoselective reduction of the C-9 keto group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00898-5