(3aS,4R,5S,6aR)-methyl [5-(tert-butyldimethylsilyl)oxy-2-oxohexahydro-cyclopenta[b]furan-4-yl]acetate | 879880-44-1

• 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)-methyl [5-(tert-butyldimethylsilyl)oxy-2-oxohexahydro-cyclopenta[b]furan-4-yl]acetate
• 英文别名: methyl 2-[(3aS,4R,5S,6aR)-5-[tert-butyl(dimethyl)silyl]oxy-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-4-yl]acetate
• CAS: 879880-44-1
• 化学式: C₁₆H₂₈O₅Si
• 分子量: 328.481
• InChiKey: ZSMYRNQJWYHKLM-LOWDOPEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4R,5S,6aR)-methyl [5-(tert-butyldimethylsilyl)oxy-2-oxohexahydro-cyclopenta[b]furan-4-yl]acetate 在 lithium hydroxide 、 硼烷四氢呋喃络合物 、 三丁基膦 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 10.5h， 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：

  [3-(tert-butyldimethylsilyl)oxy-2-methoxycabonylmethyl-5-oxocyclopentyl]acetic acid methyl ester 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以73.5%的产率得到(3aS,4R,5S,6aR)-methyl [5-(tert-butyldimethylsilyl)oxy-2-oxohexahydro-cyclopenta[b]furan-4-yl]acetate
  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.