methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5R)-5-benzyl-5-(3-methylbut-2-enyl)-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 | 159216-07-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5R)-5-benzyl-5-(3-methylbut-2-enyl)-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
• CAS: 159216-07-6
• 化学式: C₅₄H₆₉N₅O₈
• 分子量: 916.171
• InChiKey: RJCRWCRUWNOLRS-CMWBKZBGSA-N

物化性质

• 沸点：
  974.2±65.0 °C(predicted)
• 密度：
  1.170±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  67
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5R)-5-benzyl-5-(3-methylbut-2-enyl)-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 在 sodium periodate 、 四氧化锇 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 28.0h， 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：

  D-苯丙氨酸 在 sodium hydroxide 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 466.5h， 生成 methyl (2S)-2-[(5S)-5-[(5S)-5-[(5S)-5-[(5R)-5-benzyl-5-(3-methylbut-2-enyl)-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

文献信息

• A Second-Generation Synthesis of Polypyrrolinone Nonpeptidomimetics:  Prelude to the Synthesis of Polypyrrolinones on Solid Support
  作者：Amos B. Smith、Hu Liu、Ralph Hirschmann

  DOI：10.1021/ol0059293

  日期：2000.7.1

  [reaction: see text] A second-generation asymmetric synthesis of polypyrrolinones (3) has been achieved exploiting scalemic alpha-aminolactones (1) as building blocks. Imine formation between an appropriate lactone (1) and aldehyde (2), followed in turn by pyrrolinone ring construction promoted by KHMDS in the presence of 18-crown-6 and modified Swern oxidation furnished pyrrolinone aldehyde 3. This iterative

  [反应：见正文]利用垢型α-氨基内酯（1）作为结构单元，已经实现了第二代不对称合成的聚吡咯烷酮（3）。在适当的内酯（1）和醛（2）之间形成亚胺，然后依次在18-crown-6和修饰的Swern氧化作用下，由KHMDS促进吡咯烷酮环的构建，从而得到吡咯烷酮醛3。这种迭代，有效的三步法该方案为在固体载体上合成聚吡咯烷酮铺平了道路。
• US7772159B2
  申请人：——

  公开号：US7772159B2

  公开（公告）日：2010-08-10