[3-(tert-butyl-dimethylsilyl)oxy-2-carboxymethyl-5-oxo-cyclopentyl]acetic acid | 879880-42-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [3-(tert-butyl-dimethylsilyl)oxy-2-carboxymethyl-5-oxo-cyclopentyl]acetic acid
• 英文别名: 2-[(1R,2S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-(carboxymethyl)-3-oxocyclopentyl]acetic acid
• CAS: 879880-42-9
• 化学式: C₁₅H₂₆O₆Si
• 分子量: 330.453
• InChiKey: XOYYAWBSLOMGLV-UMNHJUIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-(tert-butyl-dimethylsilyl)oxy-2-carboxymethyl-5-oxo-cyclopentyl]acetic acid 在 lithium hydroxide 、 硼烷四氢呋喃络合物 、 三丁基膦 、 L-Selectride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 异丙醇 为溶剂， 反应 11.25h， 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：

  (3S,3aR,5R,6S,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-5,6-dihydroxy-octahydro-inden-1-one 在 ruthenium trichloride sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.5h， 以95%的产率得到[3-(tert-butyl-dimethylsilyl)oxy-2-carboxymethyl-5-oxo-cyclopentyl]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.