tert-butyl((2R,3R,3aS,6aS)-3-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-m-tolylbut-1-enyl)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy)dimethylsilane | 906000-88-2

• 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: tert-butyl((2R,3R,3aS,6aS)-3-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-m-tolylbut-1-enyl)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy)dimethylsilane
• 英文别名: tert-butyl((2R,3R,3aS,6aS)-3-((R,E)-3-(tert-butyldimethylsilyloxy)-4-m-tolylbut-1-enyl)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,4,6a-hexahydropentalen-2-yl)dimethylsilane；[(E,2R)-4-[(1R,2R,3aS,6aS)-2-[tert-butyl(dimethyl)silyl]oxy-5-[5-[(4-methoxyphenyl)methoxy]pentyl]-1,2,3,3a,6,6a-hexahydropentalen-1-yl]-1-(3-methylphenyl)but-3-en-2-yl]oxy-tert-butyl-dimethylsilane
• CAS: 906000-88-2
• 化学式: C₄₄H₇₀O₄Si₂
• 分子量: 719.208
• InChiKey: UYPBIQMBWZLMPS-MGAHGIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.24
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl((2R,3R,3aS,6aS)-3-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-m-tolylbut-1-enyl)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy)dimethylsilane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 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
• 作为产物：
  描述：

  (2R,E)-4-((1R,2R,3aS,6aS)-2-(tert-butyldimethylsilyloxy)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,6,6a-hexahydropentalen-1-yl)-1-m-tolylbut-3-en-2-ol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以96%的产率得到tert-butyl((2R,3R,3aS,6aS)-3-((3R,E)-3-(tert-butyldimethylsilyloxy)-4-m-tolylbut-1-enyl)-5-(5-(4-methoxybenzyloxy)pentyl)-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy)dimethylsilane
  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

文献信息

• Exploration of ω-side chain addition strategies for the syntheses of isocarbacyclin and 15R-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin
  作者：Neil A. Sheddan、Johann Mulzer

  DOI：10.1039/b611339g

  日期：——

  We describe alternative access to prostacyclin analogues by means of two ω-side chain addition strategies: Grignard reagent addition to an α,β-unsaturated Weinreb amide, followed by diastereoselective reduction of the corresponding enone system, and implementation of Seebach's alkylation chemistry. These strategies have led to the syntheses of biologically active prostacyclin analogues isocarbacyclin and 15R-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin (15R-TIC), with modest to excellent diastereoselectivity.

  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。
• Cross Metathesis as a General Strategy for the Synthesis of Prostacyclin and Prostaglandin Analogues
  作者：Neil A. Sheddan、Johann Mulzer

  DOI：10.1021/ol061141u

  日期：2006.7.1

  [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).