(R)-2-[(S)-3-tert-Butoxycarbonylamino-3-methoxycarbonyl-4-phenyl-but-(E)-ylideneamino]-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester | 178676-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[(S)-3-tert-Butoxycarbonylamino-3-methoxycarbonyl-4-phenyl-but-(E)-ylideneamino]-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester
• CAS: 178676-31-8
• 化学式: C₂₈H₄₂N₂O₆
• 分子量: 502.651
• InChiKey: IDJCBICTSOMCFP-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(S)-3-tert-Butoxycarbonylamino-3-methoxycarbonyl-4-phenyl-but-(E)-ylideneamino]-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester 在 sodium periodate 、 四氧化锇 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 104.34h， 生成 methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5S)-5-benzyl-5-[(5R)-5-(3-methylbut-2-enyl)-4-oxo-5-propan-2-yl-1H-pyrrol-3-yl]-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-5-(2-methylpropyl)-4-oxo-1H-pyrrol-3-yl]-4-oxo-5-propan-2-yl-1H-pyrrol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017
• 作为产物：
  描述：

  (R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester 在 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.0h， 生成 (R)-2-[(S)-3-tert-Butoxycarbonylamino-3-methoxycarbonyl-4-phenyl-but-(E)-ylideneamino]-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017