ethyl 2-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-[(E,3S)-3-hydroxyhex-1-en-5-ynyl]cyclopentyl]acetate | 1028041-37-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl 2-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-[(E,3S)-3-hydroxyhex-1-en-5-ynyl]cyclopentyl]acetate
• CAS: 1028041-37-3
• 化学式: C₄₇H₅₈O₅Si₂
• 分子量: 759.146
• InChiKey: PKEZGYVCGLMAIO-NUNKMNKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.41
• 重原子数：
  54
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-[(E,3S)-3-hydroxyhex-1-en-5-ynyl]cyclopentyl]acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以95%的产率得到(S,E)-1-((1R,2S,3S,5R)-3,5-bis((tert-butyldiphenylsilyl)oxy)-2-(2-hydroxyethyl)cyclopentyl)hex-1-en-5-yn-3-ol
  参考文献：
  名称：

  A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F_4t-NeuroP

  摘要：

  We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is' a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F(4t)-neuroprostane.

  DOI：

  10.1021/jo702600v
• 作为产物：
  描述：

  乙酸乙烯酯 、 ethyl 2-[(1R,2S,3S,5R)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-[(E,3R)-3-hydroxyhex-1-en-5-ynyl]cyclopentyl]acetate 在 乙酸乙烯酯 、 Amano Lipase AK 作用下， 反应 20.0h， 以508 mg的产率得到ethyl 2-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(diphenyl)silyl]oxy]-2-[(E,3S)-3-hydroxyhex-1-en-5-ynyl]cyclopentyl]acetate
  参考文献：
  名称：

  A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F_4t-NeuroP

  摘要：

  We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is' a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F(4t)-neuroprostane.

  DOI：

  10.1021/jo702600v

文献信息

• A Potential Route to Neuroprostanes and Isoprostanes: Preparation of the Four Enantiomerically Pure Diastereomers of 13-F_4t-NeuroP
  作者：Douglass F. Taber、P. Ganapati Reddy、Kyle O. Arneson

  DOI：10.1021/jo702600v

  日期：2008.5.1

  We report a potential synthetic route to the isoprostanes and the neuroprostanes that could allow ready access to each of the enantiomerically pure diastereomers of the several regioisomers of these important human metabolites. The key transformation in the synthesis is' a highly diastereoselective thermal intramolecular ene reaction. A critical observation is that the four enantiomerically pure diastereomers of an intermediate acetylenic ester are easily separated from one another. Each of these four has been carried on to a different enantiomerically pure diastereomer of 13-F(4t)-neuroprostane.