(2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester | 745016-00-6

• 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,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
• CAS: 745016-00-6
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: HEXIQOMTZDJKIR-SJORKVTESA-N

物化性质

• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2S,3R)-3-Isopropyl-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078
• 作为产物：
  描述：

  (2S,3R)-N-(叔-丁基氧羰基)-O-(叔-丁基)二甲基硅烷基-3,4-去氢-焦谷氨醇 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 jones reagent 、 copper(I) bromide dimethylsulfide complex 、 硫酸 、 氢气 、 potassium carbonate 、 丙酮 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~-20.0 ℃ 、101.33 kPa 条件下， 生成 (2S,3R)-3-Isopropyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
  参考文献：
  名称：

  Inhibitors of hepatitis C virus NS3·4A protease. Part 3: P2 proline variants

  摘要：

  We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3(.)4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P-2. These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S-2 binding pocket as the defining pharmacophore for inhibition of the NS3(.)4A enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.078