(αRS)-α-((4R,5R)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-methoxyphenylmethoxy)-5-((Z)-oct-2-enyl)cyclopent-1-enyl)-(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]-butyl)oxirane-2-methanol | 1061330-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (αRS)-α-((4R,5R)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-methoxyphenylmethoxy)-5-((Z)-oct-2-enyl)cyclopent-1-enyl)-(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]-butyl)oxirane-2-methanol
• 英文别名: [(2R,3R)-3-[4-[tert-butyl(dimethyl)silyl]oxybutyl]oxiran-2-yl]-[(4R,5R)-2-[tert-butyl(dimethyl)silyl]oxy-4-[(4-methoxyphenyl)methoxy]-5-[(Z)-oct-2-enyl]cyclopenten-1-yl]methanol
• CAS: 1061330-16-2
• 化学式: C₄₀H₇₀O₆Si₂
• 分子量: 703.163
• InChiKey: FHTVETJTFLQEDF-ZTXIOFFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.72
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (αRS)-α-((4R,5R)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-methoxyphenylmethoxy)-5-((Z)-oct-2-enyl)cyclopent-1-enyl)-(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]-butyl)oxirane-2-methanol 在 甲酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到(3R,4R,E)-2-(((2R,3R)-3-(4-hydroxybutyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-((Z)-oct-2-en-1-yl)cyclopentanone
  参考文献：
  名称：

  Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines

  摘要：

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.

  DOI：

  10.1021/ol8014804
• 作为产物：
  描述：

  (2S,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxirane-2-carbaldehyde 、 (3R,4S)-2-bromo-1-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-(methoxyphenyl)methoxy)-3-((Z)-oct-2-enyl)cyclopent-1-ene 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 3.0h， 以66%的产率得到(αRS)-α-((4R,5R)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-(4-methoxyphenylmethoxy)-5-((Z)-oct-2-enyl)cyclopent-1-enyl)-(2R,3R)-3-(4-[(1,1-dimethylethyl)dimethylsilyloxy]-butyl)oxirane-2-methanol
  参考文献：
  名称：

  Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines

  摘要：

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.

  DOI：

  10.1021/ol8014804

文献信息

• Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines
  作者：Michael E. Jung、Judith A. Berliner、Lukasz Koroniak、B. Gabriel Gugiu、Andrew D. Watson

  DOI：10.1021/ol8014804

  日期：2008.10.2

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.