ethyl 3-[[(2S)-2-methylbutanoyl]-[5-[[(2S)-2-methylbutanoyl]-[3-[[(Z,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradec-5-enoyl]amino]propyl]amino]pentyl]amino]propanoate | 207407-26-9

• 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: ethyl 3-[[(2S)-2-methylbutanoyl]-[5-[[(2S)-2-methylbutanoyl]-[3-[[(Z,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradec-5-enoyl]amino]propyl]amino]pentyl]amino]propanoate
• CAS: 207407-26-9
• 化学式: C₄₂H₇₈N₄O₇
• 分子量: 751.104
• InChiKey: FXLGKCWKBKNWPZ-NMJVSKOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  53
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-[[(2S)-2-methylbutanoyl]-[5-[[(2S)-2-methylbutanoyl]-[3-[[(Z,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradec-5-enoyl]amino]propyl]amino]pentyl]amino]propanoate 在 锂硼氢 、 pyridine-SO3 complex 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.33h， 生成 (Z,3S)-3-amino-N-[3-[[(2S)-2-methylbutanoyl]-[5-[[(2S)-2-methylbutanoyl]-(3-oxopropyl)amino]pentyl]amino]propyl]tetradec-5-enamide
  参考文献：
  名称：

  Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish

  摘要：

  Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic constituent of the skin mucus of the grammistid fish Aulacocephalus temmincki. Its absolute stereochemistry was established by chemical degradation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysis of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two diastereomers (4S)- and (4R)-1.

  DOI：

  10.1021/jo9722461
• 作为产物：
  描述：

  N-(2-氰乙基)-1,5-二氨基戊烷 在 platinum(IV) oxide 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 3-[[(2S)-2-methylbutanoyl]-[5-[[(2S)-2-methylbutanoyl]-[3-[[(Z,3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]tetradec-5-enoyl]amino]propyl]amino]pentyl]amino]propanoate
  参考文献：
  名称：

  Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish

  摘要：

  Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic constituent of the skin mucus of the grammistid fish Aulacocephalus temmincki. Its absolute stereochemistry was established by chemical degradation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysis of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two diastereomers (4S)- and (4R)-1.

  DOI：

  10.1021/jo9722461

文献信息

• Absolute Structure and Total Synthesis of Lipogrammistin-A, a Lipophilic Ichthyotoxin of the Soapfish
  作者：Hiroyuki Onuki、Kei Ito、Yoshimasa Kobayashi、Nobuaki Matsumori、Kazuo Tachibana、Nobuhiro Fusetani

  DOI：10.1021/jo9722461

  日期：1998.6.1

  Lipogrammistin-A (Ib) was isolated as an ichthyotoxic and hemolytic constituent of the skin mucus of the grammistid fish Aulacocephalus temmincki. Its absolute stereochemistry was established by chemical degradation and total synthesis. The stereochemistry of the 2-methylbutyryl moieties attached to N9 and N15 was determined to be S by HPLC analysis of a diastereomeric derivative. The stereochemistry of the remaining C4 position was elucidated to be S by a total synthesis of the two diastereomers (4S)- and (4R)-1.