(3aS,4R,5S,6aR)-[5-(tert-butyldimethylsilyl)oxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]acetic acid | 879880-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,4R,5S,6aR)-[5-(tert-butyldimethylsilyl)oxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]acetic acid
• 英文别名: 2-[(3aS,4R,5S,6aR)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]acetic acid
• CAS: 879880-45-2
• 化学式: C₁₅H₂₆O₅Si
• 分子量: 314.454
• InChiKey: LGZJAWDTFAJTIM-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,6aR)-[5-(tert-butyldimethylsilyl)oxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]acetic acid 在 硼烷四氢呋喃络合物 、 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (3aS,4R,5S,6aR)-hexahydro-5-(tert-butyldimethylsilyl)oxy-4-(2-(2-nitrophenylselanyl)-ethyl)-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Total Synthesis of 8,12-iso-iPF_3α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center

  摘要：

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.

  DOI：

  10.1021/jo051916x
• 作为产物：
  描述：

  (1S,6R,7S)-7-[(tert-butyldimethylsilyl)oxy]bicyclo[4.3.0]non-3-en-9-one 在 ruthenium trichloride 、 四氧化锇 lithium hydroxide 、 sodium periodate 、 十二/十四烷基二甲基氧化胺 、 L-Selectride 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 水 、 异丙醇 、 乙腈 、 叔丁醇 为溶剂， 反应 8.75h， 生成 (3aS,4R,5S,6aR)-[5-(tert-butyldimethylsilyl)oxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl]acetic acid
  参考文献：
  名称：

  Total Synthesis of 8,12-iso-iPF_3α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center

  摘要：

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.

  DOI：

  10.1021/jo051916x

文献信息

• Total Synthesis of 8,12-<i>iso</i>-iPF₃_α-VI, an EPA-Derived Isoprostane:  Stereoselective Introduction of the Fifth Asymmetric Center
  作者：Sheila H. Jacobo、Chih-Tsung Chang、Gue-Jae Lee、John A. Lawson、William S. Powell、Domenico Pratico、Garret A. FitzGerald、Joshua Rokach

  DOI：10.1021/jo051916x

  日期：2006.2.1

  A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF(3 alpha)-VI 10, was performed using this approach.