methyl (S,E)-7-{(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-[(Z)-oct-2-enyl]cyclopentyl}-5-(tert-butyldimethylsilyloxy)hept-6-enoate | 1025719-34-9

• 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: methyl (S,E)-7-{(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-[(Z)-oct-2-enyl]cyclopentyl}-5-(tert-butyldimethylsilyloxy)hept-6-enoate
• CAS: 1025719-34-9
• 化学式: C₃₉H₇₈O₅Si₃
• 分子量: 711.302
• InChiKey: FQLRSKQDKCJTNU-QJKKUINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.22
• 重原子数：
  47.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (S,E)-7-{(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-[(Z)-oct-2-enyl]cyclopentyl}-5-(tert-butyldimethylsilyloxy)hept-6-enoate 在 四丁基氟化铵 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以32%的产率得到ent-5-epi-F_2t-isoprostane
  参考文献：
  名称：

  A Cross-Metathesis Route to the 5-F₂-Isoprostanes

  摘要：

  A library of eight 5-F-2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and alpha,beta-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F-2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.

  DOI：

  10.1021/jo702702s
• 作为产物：
  描述：

  、 n-溴代已基三苯基膦 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以43 mg的产率得到methyl (S,E)-7-{(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-[(Z)-oct-2-enyl]cyclopentyl}-5-(tert-butyldimethylsilyloxy)hept-6-enoate
  参考文献：
  名称：

  A Cross-Metathesis Route to the 5-F₂-Isoprostanes

  摘要：

  A library of eight 5-F-2-isoprostanes was prepared through a ring-opening metathesis/cross-metathesis protocol between functionalized bicyclo[3.2.0]heptenes, ethylene, and alpha,beta-unsaturated ketones. This sequence provided racemic enones in a regio- and stereoselective fashion that could be converted to enantiomerically enriched allylic alcohols through a catalyst-controlled asymmetric reduction. Completion of the sidechains, followed by global deprotection, resulted in a stereodivergent route to eight enantiomerically enriched 5-F-2 isoprostanes. Overall, the synthesis of this library of known and anticipated lipid oxidation metabolites was achieved in 10 steps from commercially available 4-hydroxy-2-cyclopentenone.

  DOI：

  10.1021/jo702702s