(1S,2S,3S,4R)-3-Carboxy-2-((phenylsulfonyl)amino)bicyclo<2.2.1>heptane | 132747-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S,3S,4R)-3-Carboxy-2-((phenylsulfonyl)amino)bicyclo<2.2.1>heptane
• 英文别名: (1R,2S,3S,4S)-3-(benzenesulfonamido)bicyclo[2.2.1]heptane-2-carboxylic acid
• CAS: 132747-46-7
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: GRUQUQTZGLGYDF-URBCHYCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4R)-3-Carboxy-2-((phenylsulfonyl)amino)bicyclo<2.2.1>heptane 在 sodium tetrahydroborate 、 草酰氯 、 碘 、 二甲基亚砜 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 生成 N-((1S,2S,3S,4R)-3-Formyl-bicyclo[2.2.1]hept-2-yl)-benzenesulfonamide
  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：

  (1R,2S,3S,4S)-3-Carbamoyl-2-carboxybicyclo<2.2.1>heptane 、 苯磺酰氯 在 sodium hydroxide 、 sodium hypochlorite 作用下， 生成 (1S,2S,3S,4R)-3-Carboxy-2-((phenylsulfonyl)amino)bicyclo<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

文献信息

• OHTANI, MITSUAKI;MATSUURA, TAKAHARU;WATANABE, FUMIHIKO;NARISADA, MASAYUKI, J. ORG. CHEM., 56,(1991) N, C. 2122-2127
  作者：OHTANI, MITSUAKI、MATSUURA, TAKAHARU、WATANABE, FUMIHIKO、NARISADA, MASAYUKI

  DOI：——

  日期：——
• JPH06271521A
  申请人：——

  公开号：JPH06271521A

  公开（公告）日：1994-09-27
• JPH06271527A
  申请人：——

  公开号：JPH06271527A

  公开（公告）日：1994-09-27
• Enantioselective synthesis of S-1452, an orally active potent thromboxane A2 receptor antagonist
  作者：Mitsuaki Ohtani、Takaharu Matsuura、Fumihiko Watanabe、Masayuki Narisada

  DOI：10.1021/jo00006a030

  日期：1991.3

  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.