(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(R)-(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester | 131466-58-5

• 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: (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(R)-(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester
• 英文别名: (1R,2S,3R,4S)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(R)-(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester
• CAS: 131466-58-5；132674-12-5；132747-50-3
• 化学式: C₂₅H₂₄O₇
• 分子量: 436.461
• InChiKey: UZVWPFGVBDUPHZ-DYNVPVJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(R)-(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester 在 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 氯甲酸乙酯 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.2h， 生成 (1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane
  参考文献：
  名称：

  Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist

  摘要：

  An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.

  DOI：

  10.1021/jo00006a030
• 作为产物：
  描述：

  lithium p-methoxybenzyl (R)-mandelate 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 生成 (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(R)-(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester 、 (1R,2S,3R,4S)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-[(4-methoxy-benzyloxycarbonyl)-phenyl-methyl] ester
  参考文献：
  名称：

  Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist

  摘要：

  An efficient and extremely practical enantioselective fission of pro-chiral bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride was applied to the asymmetric synthesis of the potent and orally active thromboxane A2 (TXA2) receptor antagonist, S-1452. The lithium salt of (R)-(-)-benzylmandelate was employed as a chiral ligand, giving a crystalline key intermediate 3 of which the chemical purity was 100.0% after crystallization. Epimerization and the methanolysis process of 3 afforded the half ester 4, which was transformed into S-1452.

  DOI：

  10.1021/jo00006a030