(5Z)-7-{(1R,2R,5S)-2-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-5-hydroxy-cyclopent-3-enyl}-hept-5-enoic acid methyl ester | 587869-79-2

• 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-{(1R,2R,5S)-2-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-5-hydroxy-cyclopent-3-enyl}-hept-5-enoic acid methyl ester
• 英文别名: methyl (Z)-7-[(1R,2R,5S)-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-hydroxycyclopent-3-en-1-yl]hept-5-enoate
• CAS: 587869-79-2
• 化学式: C₂₇H₄₈O₄Si
• 分子量: 464.761
• InChiKey: QSLMPXBXDSOVOV-LIMRVOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z)-7-{(1R,2R,5S)-2-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-5-hydroxy-cyclopent-3-enyl}-hept-5-enoic acid methyl ester 在 三丁基膦 、 双氧水 、 溶剂黄146 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 82.0h， 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
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 (5Z)-7-{(1R,2R,5S)-2-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-5-hydroxy-cyclopent-3-enyl}-hept-5-enoic acid methyl ester
  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

• A → J Prostaglandin Swap:  A New Tactic for Cyclopentenone Prostaglandin Synthesis
  作者：Giuseppe Zanoni、Francesca Castronovo、Eleonora Perani、Giovanni Vidari

  DOI：10.1021/jo034501p

  日期：2003.8.1

  A practical methodology for the synthesis of J-type prostaglandins has been developed starting from the well-consolidated approaches established for the synthesis of A-type prostaglandins. An efficient 1,3-allylic transposition of the C-9 hydroxyl group of intermediate 4 furnished the advanced precursor 5 for J(2) synthesis. Our optimized A-J swap protocol employed selenium chemistry, involving the [2,3] sigmatropic rearrangement of secondary allylic selenoxide 11a.