(R)-2-((2R,3S)-2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)-tetrahydrofuran-3-carboxamido)-3-methylbutanoic acid | 1149670-06-3

• 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: (R)-2-((2R,3S)-2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)-tetrahydrofuran-3-carboxamido)-3-methylbutanoic acid
• CAS: 1149670-06-3
• 化学式: C₂₁H₂₉BrN₂O₆
• 分子量: 485.375
• InChiKey: OGBOLEUNVRZFOG-ZOCZFRKYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  663.8±55.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-2-((2R,3S)-2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)-tetrahydrofuran-3-carboxamido)-3-methylbutanoic acid 、 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到methyl (R)-2-((2R,3S)-2-(4-bromophenyl)-3-((R)-2-((2R,3S)-2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)-tetrahydrofuran-3-carboxamido)-3-methylbutanamido)-tetrahydrofuran-3-carboxamido)-3-methylbutanoate
  参考文献：
  名称：

  Stable Right- and Left-Handed Peptide Helices containing C^α-Tetrasubstituted α-Amino Acids

  摘要：

  Short peptidomimetics with stable secondary structures in solution are of interest for applications in chemistry, biology, and medicine. One way to rigidify the backbone of a peptide is the use of cyclic C-alpha-tetrasubstituted alpha-amino acids (TAAs) like compound 14. The structures resulting from the incorporation of this unnatural amino acid into peptides were investigated. In total, 13 different peptides with a length of up to eight residues and alternating sequences of TAA 14 and (S)- or (R)-valine were synthesized. Their structures were characterized by X-ray diffraction analysis and NMR and CD measurements showing that the all-S-backbone-configured peptides 5 and 6 (SS)(2-3) form fight-handed 3(10)-helices, while the all-R-configured peptides 11-13 (RR)(2-4) form left-handed 3(10)-helices in the solid state and solution.

  DOI：

  10.1021/jo900222g
• 作为产物：
  描述：

  methyl (2R)-2-(2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)tetrahydrofuran-3-carboxamido)-3-methylbutanoate 在 lithium hydroxide 、 水 作用下， 以 乙腈 为溶剂， 以94%的产率得到(R)-2-((2R,3S)-2-(4-bromophenyl)-3-(tert-butoxycarbonylamino)-tetrahydrofuran-3-carboxamido)-3-methylbutanoic acid
  参考文献：
  名称：

  Stable Right- and Left-Handed Peptide Helices containing C^α-Tetrasubstituted α-Amino Acids

  摘要：

  Short peptidomimetics with stable secondary structures in solution are of interest for applications in chemistry, biology, and medicine. One way to rigidify the backbone of a peptide is the use of cyclic C-alpha-tetrasubstituted alpha-amino acids (TAAs) like compound 14. The structures resulting from the incorporation of this unnatural amino acid into peptides were investigated. In total, 13 different peptides with a length of up to eight residues and alternating sequences of TAA 14 and (S)- or (R)-valine were synthesized. Their structures were characterized by X-ray diffraction analysis and NMR and CD measurements showing that the all-S-backbone-configured peptides 5 and 6 (SS)(2-3) form fight-handed 3(10)-helices, while the all-R-configured peptides 11-13 (RR)(2-4) form left-handed 3(10)-helices in the solid state and solution.

  DOI：

  10.1021/jo900222g