(2S,3R)-2-{[3-endo-(1-(tert-butoxycarbonyl)-2-phenylethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carbonyl]amino}-4-methylpentanoic acid benzyl ester

• 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)-2-{[3-endo-(1-(tert-butoxycarbonyl)-2-phenylethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carbonyl]amino}-4-methylpentanoic acid benzyl ester
• 英文别名: benzyl (2S)-4-methyl-2-[[(1S,2S,3R,4R)-3-[[(2S)-1-[(2-methylpropan-2-yl)oxy]-1-oxo-3-phenylpropan-2-yl]carbamoyl]bicyclo[2.2.1]heptane-2-carbonyl]amino]pentanoate
• 化学式: C₃₅H₄₆N₂O₆
• 分子量: 590.76
• InChiKey: WQECSTHWSQVBRL-FSIJYMTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-苯基丙氨酸叔丁酯 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 26.0h， 生成 (2S,3R)-2-{[3-endo-(1-(tert-butoxycarbonyl)-2-phenylethylcarbamoyl)bicyclo[2.2.1]heptane-2-endo-carbonyl]amino}-4-methylpentanoic acid benzyl 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+

文献信息

• General Synthesis of Unsymmetrical Norbornane Scaffolds as Inducers for Hydrogen Bond Interactions in Peptides^,
  作者：Christian P. R. Hackenberger、Ingo Schiffers、Jan Runsink、Carsten Bolm

  DOI：10.1021/jo030295+

  日期：2004.2.1

  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.