(5Z)-7-{(1S,5R)-5-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid | 587869-89-4

• 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: (5Z)-7-{(1S,5R)-5-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid
• 英文别名: (Z)-7-[(1S,5R)-5-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
• CAS: 587869-89-4
• 化学式: C₂₆H₄₄O₄Si
• 分子量: 448.718
• InChiKey: NFENWDBWGZJZOE-LJVGVLHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z)-7-{(1S,5R)-5-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以88%的产率得到前列腺素 J2
  参考文献：
  名称：

  First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

  摘要：

  Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.

  DOI：

  10.1021/jo034502h
• 作为产物：
  描述：

  [3aR(3aα,4α,5β,6aα)]-(-)-5-(苯甲酰氧基)六氢-2-氧代-2H-环戊并[b]呋喃-4-甲醛 在 咪唑 、 4-二甲氨基吡啶 、 乙醇 、 三丁基膦 、 (-)-(S)-BINAL-H 、 potassium tert-butylate 、 双氧水 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 134.25h， 生成 (5Z)-7-{(1S,5R)-5-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-4-oxo-cyclopent-2-enyl}-hept-5-enoic acid
  参考文献：
  名称：

  First Enantioselective Total Synthesis of (8S,12R,15S)-Prostaglandin J₂

  摘要：

  Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.

  DOI：

  10.1021/jo034502h

文献信息

• First Enantioselective Total Synthesis of (8<i>S</i>,12<i>R</i>,15<i>S</i>)-Prostaglandin J₂
  作者：Giuseppe Zanoni、Alessio Porta、Quintino De Toma、Francesca Castronovo、Giovanni Vidari

  DOI：10.1021/jo034502h

  日期：2003.8.1

  Enantioselective synthesis of natural PGJ(2) has been accomplished for the first time starting from the commercially available enantiopure aldehyde 7 in 10% overall yield. The key reaction was a novel prostaglandin class interconversion, i.e., an allylic 1,3-transposition across alcohol 9 derived from compound 14 in 73% overall yield. In principle, the unnatural enantiomer of PGJ(2) could be obtained starting from the commercially available enantiopure monobenzoate 7a following our strategy.