(S)-tert-butyl 2-((2S,3R,4E)-1-((S)-2-benzamido-6-(2,3-bis-(tert-butoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate | 1403324-67-3

• 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: (S)-tert-butyl 2-((2S,3R,4E)-1-((S)-2-benzamido-6-(2,3-bis-(tert-butoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate
• 英文别名: tert-butyl (2S)-2-[[(2S,3R,4E)-1-[(2S)-2-benzamido-6-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]hexanoyl]-4-ethylidene-3-methylpyrrolidine-2-carbonyl]amino]-4-methylpentanoate
• CAS: 1403324-67-3
• 化学式: C₄₂H₆₆N₆O₉
• 分子量: 799.021
• InChiKey: ZQZKDRYAHWPRDF-ZZJOKWFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  57
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  194
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-((2S,3R,4E)-1-((S)-2-benzamido-6-(2,3-bis-(tert-butoxycarbonyl)guanidino)hexanoyl)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以67%的产率得到lucentamycin A
  参考文献：
  名称：

  仿生钯催化分子内 C(sp3)-H 活化用于脯氨酸天然产物的集体合成

  摘要：

  仿生钯 (II) 催化的通过 C-H 活化对含有碘乙烯部分的氨基酸衍生物进行分子内环化，可以快速获得具有环外双键的各种功能化脯氨酸衍生物。这种功能化的脯氨酸被用作几种天然产物全合成的中间体：光亮霉素 A、巴木霉素、氧代梅霉素和氧代原霉素。

  DOI：

  10.1002/anie.202207088
• 作为产物：
  描述：

  (S)-tert-butyl 2-((2S,3R,E)-4-ethylidene-3-methylpyrrolidine-2-carboxamido)-4-methylpentanoate 在 二乙胺 、 三乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (S)-tert-butyl 2-((2S,3R,4E)-1-((S)-2-benzamido-6-(2,3-bis-(tert-butoxycarbonyl)guanidino)hexanoyl)-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

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.
• Bioinspired Palladium‐Catalyzed Intramolecular C(sp ³ )−H Activation for the Collective Synthesis of Proline Natural Products
  作者：Quan‐Zhe Li、Si‐Hua Hou、Jun‐Chen Kang、Peng‐Fei Lian、Yu Hao、Chao Chen、Jia Zhou、Tong‐Mei Ding、Shu‐Yu Zhang

  DOI：10.1002/anie.202207088

  日期：2022.8.15

  Bioinspired palladium(II)-catalyzed intramolecular cyclization of amino acid derivatives containing a vinyl iodide moiety by C−H activation enabled rapid access to a wide range of functionalized proline derivatives with an exocyclic double bond. Such functionalized prolines were used as intermediates for the total synthesis of several natural products: lucentamycin A, barmumycin, oxotomaymycin, and

  仿生钯 (II) 催化的通过 C-H 活化对含有碘乙烯部分的氨基酸衍生物进行分子内环化，可以快速获得具有环外双键的各种功能化脯氨酸衍生物。这种功能化的脯氨酸被用作几种天然产物全合成的中间体：光亮霉素 A、巴木霉素、氧代梅霉素和氧代原霉素。