(2S,3R)-3-endo-[1-(1-methoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]bicyclo[2.2.1]heptane-2-endo-carboxylic acid | 660439-30-5

• 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: (2S,3R)-3-endo-[1-(1-methoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]bicyclo[2.2.1]heptane-2-endo-carboxylic acid
• CAS: 660439-30-5
• 化学式: C₂₂H₂₈N₂O₆
• 分子量: 416.474
• InChiKey: AHMFWGDVPLRYED-UIAIQNDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  121.8
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  HPheGlyOBn 、 (2S,3R)-3-endo-[1-(1-methoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]bicyclo[2.2.1]heptane-2-endo-carboxylic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以71%的产率得到(2S,3R)-[2-({3-endo-[1-(benzyloxycarbonyl-methylcarbamoyl)-2-phenyl-ethylcarbamoyl]bicyclo[2.2.1]heptane-2-endo-carbonyl}amino)-3-phenyl-propionylamino]propionic acid methyl ester
  参考文献：
  名称：

  General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,

  摘要：

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.

  DOI：

  10.1021/jo030295+
• 作为产物：
  描述：

  (2R,3S)-3-endo-benzyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 13.0h， 生成 (2S,3R)-3-endo-[1-(1-methoxycarbonyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]bicyclo[2.2.1]heptane-2-endo-carboxylic acid
  参考文献：
  名称：

  General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,

  摘要：

  Starting from readily accessible endo-cis-(2S,3R)-norbornene dicarboxylic acid benzyl monoester, a general and efficient synthetic approach toward unsymmetrical two-stranded peptidic structures was developed. In these structures the peptide strands are oriented in a parallel geometry. Their synthesis is easily applicable to a variety of amino acids and peptides. Specifically, a norbornane template as molecular scaffold induces hydrogen bonding between the adjacent peptide strands. The specific hydrogen bonding patterns between these strands were revealed by detailed NMR analysis including TOCSY/NOE experiments.

  DOI：

  10.1021/jo030295+