tert-butyl (2S)-2-[[(E,2S,3R)-4-(hydroxymethyl)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]amino]-4-methylpentanoate | 1403324-69-5

• 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 (2S)-2-[[(E,2S,3R)-4-(hydroxymethyl)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]amino]-4-methylpentanoate
• CAS: 1403324-69-5
• 化学式: C₂₃H₄₂N₂O₆
• 分子量: 442.596
• InChiKey: GRFWVYFNTOQHSR-CSTMUPAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[[(E,2S,3R)-4-(hydroxymethyl)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]amino]-4-methylpentanoate 在 potassium carbonate 、 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 44.5h， 生成 (S)-tert-butyl 2-((2S,3R,E)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis and Structural Revision of Lucentamycin A

  摘要：

  Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Gamer's aldehyde.

  DOI：

  10.1021/jo301723y
• 作为产物：
  描述：

  在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 氘代甲醇-d 为溶剂， 反应 0.75h， 以84%的产率得到tert-butyl (2S)-2-[[(E,2S,3R)-4-(hydroxymethyl)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis and Structural Revision of Lucentamycin A

  摘要：

  Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Gamer's aldehyde.

  DOI：

  10.1021/jo301723y

文献信息

• Total Synthesis and Structural Revision of Lucentamycin A
  作者：Sujeewa Ranatunga、Chih-Hang Anthony Tang、Chih-Chi Andrew Hu、Juan R. Del Valle

  DOI：10.1021/jo301723y

  日期：2012.11.2

  Lucentamycin A is a marine-derived peptide natural product harboring a unique 4-ethylidene-3-methylproline (Emp) subunit. The proposed structure of lucentamycin A and the core Emp residue have recently been called into question through synthesis. Here, we report the first total synthesis of lucentamycin A, which confirms that the ethylidene substituent in Emp bears an E geometry, in contrast to the originally assigned Z configuration. Synthesis of the desired (E)-Emp subunit required the implementation of a novel strategy starting from Gamer's aldehyde.