(2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester | 314082-73-0

• 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: (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
• CAS: 314082-73-0
• 化学式: C₂₅H₃₁NO₅
• 分子量: 425.525
• InChiKey: VYTQHKRARLZPLS-QUCQDJGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以87%的产率得到(2S,4R)-4-Phenethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  Highly potent and selective peptide-based inhibitors of the hepatitis C virus serine protease: towards smaller inhibitors

  摘要：

  Structure-activity studies on a hexapeptide N-terminal cleavage product of a dodecamer substrate led to the identification of very potent and highly specific inhibitors of the HCV NS3 protease/NS4A cofactor peptide complex. The largest increase in potency was accomplished by the introduction of a (4R)-naphthalen-1-yl-4-methoxy substituent to the P2 proline. N-Terminal truncation resulted in tetrapeptides containing a C-terminal carboxylic acid, which exhibited low micromolar activity against the HCV serine protease. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00465-0
• 作为产物：
  描述：

  benzyl (2S,4R)-4-allyl-1N-tert-butoxycarbonylpyrrolidine-2-carboxylate 在 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 水 、 叔丁醇 为溶剂， 生成 (2S,4S)-4-(2-Hydroxy-2-phenyl-ethyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester
  参考文献：
  名称：

  Highly potent and selective peptide-based inhibitors of the hepatitis C virus serine protease: towards smaller inhibitors

  摘要：

  Structure-activity studies on a hexapeptide N-terminal cleavage product of a dodecamer substrate led to the identification of very potent and highly specific inhibitors of the HCV NS3 protease/NS4A cofactor peptide complex. The largest increase in potency was accomplished by the introduction of a (4R)-naphthalen-1-yl-4-methoxy substituent to the P2 proline. N-Terminal truncation resulted in tetrapeptides containing a C-terminal carboxylic acid, which exhibited low micromolar activity against the HCV serine protease. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00465-0