(3aR,4R,5R,6aS)-benzoic acid 4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester | 587869-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3aR,4R,5R,6aS)-benzoic acid 4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• 英文别名: (3aR,4R,5R,6aS)-4-((S,E)-3-((tert-Butyldimethylsilyl)oxy)oct-1-en-1-yl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate；[(3aR,4R,5R,6aS)-4-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 587869-81-6
• 化学式: C₂₈H₄₂O₅Si
• 分子量: 486.724
• InChiKey: HCFDVFAZKOSMJZ-FRVOEXHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (3aR,4R,5R,6aS)-benzoic acid 4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 在 三丁基膦 、 氢氟酸 、 potassium tert-butylate 、 双氧水 、 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 、 乙腈 为溶剂， 反应 131.25h， 生成 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 、 (-)-(S)-BINAL-H 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (3aR,4R,5R,6aS)-benzoic acid 4-[(1E,3S)-3-(tert-butyl-dimethylsilanyloxy)-oct-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl 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

• 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.