methyl (S,E)-7-[(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate | 1025719-32-7

• 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-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate
• CAS: 1025719-32-7
• 化学式: C₃₃H₆₈O₆Si₃
• 分子量: 645.156
• InChiKey: QHPSDAWZQISNJP-WADDSUIGSA-N

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-(2-hydroxyethyl)cyclopentyl]-5-(tert-butyldimethylsilyloxy)hept-6-enoate 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 生成
  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：

  在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以89.9 mg的产率得到methyl (S,E)-7-[(1R,2S,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-(2-hydroxyethyl)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