methyl 8-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]octanoate | 628298-91-9

• 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 8-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]octanoate
• CAS: 628298-91-9
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: VGFKBSUKEZNUFU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 8-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]octanoate 在 吡啶 、 正丁基锂 、 氢氟酸 、 甲基锂 、 sodium chloride 、 calcium chloride 、 lipase 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 24.0h， 生成 16-epi-phytoprostane E1
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042
• 作为产物：
  描述：

  methyl 8-[(3R)-3-acetyloxy-5-oxocyclopenten-1-yl]octanoate 在 4-二甲氨基吡啶 、 胍 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 8-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]octanoate
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042

文献信息

• First total synthesis of the E type I phytoprostanes
  作者：Ana R. Rodrı́guez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2003.08.042

  日期：2003.9

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.