tert-butyl N-[(2S)-3-hydroxy-4-[(2S)-2-(2-naphthalen-2-ylethylcarbamoyl)pyrrolidin-1-yl]-4-oxo-1-phenylmethoxybutan-2-yl]carbamate | 1207757-64-9

• 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: tert-butyl N-[(2S)-3-hydroxy-4-[(2S)-2-(2-naphthalen-2-ylethylcarbamoyl)pyrrolidin-1-yl]-4-oxo-1-phenylmethoxybutan-2-yl]carbamate
• CAS: 1207757-64-9
• 化学式: C₃₃H₄₁N₃O₆
• 分子量: 575.705
• InChiKey: FXTCOXQKZUBFTM-ASYYUYISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-3-hydroxy-4-[(2S)-2-(2-naphthalen-2-ylethylcarbamoyl)pyrrolidin-1-yl]-4-oxo-1-phenylmethoxybutan-2-yl]carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Convergent Synthesis of α-Ketoamide Inhibitors of Pin1

  摘要：

  A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl2 to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC50 values of 100 and 200 mu W were surprisingly weak for Pin1 peptidyl prolyl isomerase.

  DOI：

  10.1021/ol9027013
• 作为产物：
  描述：

  (2S)-N-(2-naphthalen-2-ylethyl)pyrrolidine-2-carboxamide 、 tert-butyl N-[(2S)-3-hydroxy-4,4,4-tris(methylsulfanyl)-1-phenylmethoxybutan-2-yl]carbamate 在 水 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以80%的产率得到tert-butyl N-[(2S)-3-hydroxy-4-[(2S)-2-(2-naphthalen-2-ylethylcarbamoyl)pyrrolidin-1-yl]-4-oxo-1-phenylmethoxybutan-2-yl]carbamate
  参考文献：
  名称：

  Convergent Synthesis of α-Ketoamide Inhibitors of Pin1

  摘要：

  A convergent synthesis of alpha-ketoamide inhibitors of Pin1 is described. An alpha-hydroxyorthothioester derivative of Ser was reacted directly with an amine synthon. The reaction was catalyzed by HgO and HgCl2 to form alpha-hydroxyamide. Thus, hydrolysis and coupling were combined in one step with 80% yield. Two diastereomers of a phospho-Ser-Pro alpha-ketoamide analogue were synthesized. The IC50 values of 100 and 200 mu W were surprisingly weak for Pin1 peptidyl prolyl isomerase.

  DOI：

  10.1021/ol9027013