prop-2-enyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[[(2S,3S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopentan-2-yl]carbamoylamino]hexanoate | 1042724-85-5

• 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: prop-2-enyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[[(2S,3S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopentan-2-yl]carbamoylamino]hexanoate
• CAS: 1042724-85-5
• 化学式: C₃₅H₄₇N₃O₇
• 分子量: 621.774
• InChiKey: MOIVFOXFMKVNHV-HDXYBINASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[[(2S,3S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopentan-2-yl]carbamoylamino]hexanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到(2S,3S)-2-[[(2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-1-oxo-1-prop-2-enoxyhexan-2-yl]carbamoylamino]-3-methylpentanoic acid
  参考文献：
  名称：

  Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A

  摘要：

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

  DOI：

  10.1021/ol801064d
• 作为产物：
  描述：

  brunsvicamide A 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 prop-2-enyl (2S)-6-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[[(2S,3S)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopentan-2-yl]carbamoylamino]hexanoate
  参考文献：
  名称：

  Solid-Support Based Total Synthesis and Stereochemical Correction of Brunsvicamide A

  摘要：

  A total synthesis of the cyanobacterial metabolite brunsvicamide A and the correction of its originally assigned stereochemistry are reported. Key elements were the construction of a urea building block, peptide elongation on solid phase, and on-resin cyclization of the peptide chain, with good overall yield. Detailed structural investigations uncovered that brunsvicamide A features a previously undetected D-lysine residue in its backbone, setting the foundation for all further investigations in this compound class.

  DOI：

  10.1021/ol801064d