(S)-2-{(R)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid methyl ester | 477526-92-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-2-{(R)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid methyl ester
• CAS: 477526-92-4
• 化学式: C₃₄H₄₈N₄O₈
• 分子量: 640.777
• InChiKey: XAIXFFXHHHCQJX-OUDAGIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172.16
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(R)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid methyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 potassium bromide 作用下， 以80%的产率得到methyl (2S)-3-methyl-2-[[(2R)-4-methyl-2-[[(3S)-2-oxo-3-[[(2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]pentanoyl]amino]pentanoyl]amino]butanoate
  参考文献：
  名称：

  Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes

  摘要：

  Extension of the previously reported modification of Passerini multicomponent reaction (involving condensation with N-Boc-alpha-aminoaldehydes followed by a deprotection-transacylation step) to alpha-aminoacid derived carboxylic or isocyanide components, allowed the highly convergent and short synthesis of complex peptidomimetic structures, including known potent inhibitors of serine proteases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00728-1
• 作为产物：
  描述：

  D-亮氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙酸酐 为溶剂， 反应 104.0h， 生成 (S)-2-{(R)-2-[(S)-3-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes

  摘要：

  Extension of the previously reported modification of Passerini multicomponent reaction (involving condensation with N-Boc-alpha-aminoaldehydes followed by a deprotection-transacylation step) to alpha-aminoacid derived carboxylic or isocyanide components, allowed the highly convergent and short synthesis of complex peptidomimetic structures, including known potent inhibitors of serine proteases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00728-1