(2S)-N-[(2S)-1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentylamino]-1-oxo-3-phenylpropan-2-yl]-2-amino-4-methylpentanamide | 392658-38-7

• 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: (2S)-N-[(2S)-1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentylamino]-1-oxo-3-phenylpropan-2-yl]-2-amino-4-methylpentanamide
• CAS: 392658-38-7
• 化学式: C₃₀H₄₈N₆O₄S
• 分子量: 588.815
• InChiKey: CHDIRMQLJRQMFC-CPHHOOCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-N-[(2S)-1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentylamino]-1-oxo-3-phenylpropan-2-yl]-2-amino-4-methylpentanamide 在 四丁基氟化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 {5-(4-benzoyl-phenyl)-1S-benzyl-2R-hydroxy-4R-[3-methyl-1S-(1-{5-[5-(2-oxo-(3aR,6aS)-hexahydro-thieno[3,4-d]imidazol-6S-yl)-pentanoylamino]-pentylcarbamoyl}-2S-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Photoreactive Peptidomimetic γ-Secretase Inhibitors

  摘要：

  The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.

  DOI：

  10.1021/jo0486948
• 作为产物：
  描述：

  5-(氨基维生素)戊胺 在 三氟乙酸 作用下， 生成 (2S)-N-[(2S)-1-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]pentylamino]-1-oxo-3-phenylpropan-2-yl]-2-amino-4-methylpentanamide
  参考文献：
  名称：

  Stereoselective Synthesis of Photoreactive Peptidomimetic γ-Secretase Inhibitors

  摘要：

  The first asymmetric synthesis of novel, potent photoreactive gamma-secretase inhibitors 2 and 3 has been accomplished. Two stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing gamma-secretase activity in the plasma membrane of intact cells.

  DOI：

  10.1021/jo0486948