5-{(3aS,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-m-tolyl-but-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid | 906000-89-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-{(3aS,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-m-tolyl-but-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid
• CAS: 906000-89-3
• 化学式: C₃₆H₆₀O₄Si₂
• 分子量: 613.041
• InChiKey: UYJPSQBFDKVUFE-ZMSPMHBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-{(3aS,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-m-tolyl-but-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-((3aS,5R,6R,6aS)-5-hydroxy-6-((3R,E)-3-hydroxy-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanoic acid
  参考文献：
  名称：

  Exploration of ω-side chain addition strategies for the syntheses of isocarbacyclin and 15R-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin

  摘要：

  我们描述了通过两种ω侧链添加策略获得前列腺素类类似物的替代途径：将格氏试剂添加到α,β-不饱和韦纳布酰胺中，然后对相应的酮系统进行立体选择性还原，并实施Seebach的烷基化化学。这些策略已经导致生物活性前列腺素类类似物异羧基前列腺素和15R-16-(m-甲基苯基)-17,18,19,20-四氟异羧基前列腺素（15R-TIC）的合成，具有适度到优秀的立体选择性。

  DOI：

  10.1039/b611339g
• 作为产物：
  描述：

  5-{(3aS,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-m-tolyl-but-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentan-1-ol 生成 5-{(3aS,5R,6R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-m-tolyl-but-1-enyl]-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl}-pentanoic acid
  参考文献：
  名称：

  Cross Metathesis as a General Strategy for the Synthesis of Prostacyclin and Prostaglandin Analogues

  摘要：

  [GRAPHICS]A cross metathesis ( CM) approach has been successfully applied to introduce fully functionalized omega-side chain appendages of various prostacyclin and prostaglandin analogues, resulting in high (E)-selectivities for the C13-C14 double bond and leading to the total syntheses of isocarbacyclin, 15R-TIC, carbacyclin, and PGF(2 alpha) and the formal syntheses of 15-deoxy-TIC and PGJ(2).

  DOI：

  10.1021/ol061141u