4-(Benzyl-benzyloxycarbonylmethyl-amino)-butyric acid tert-butyl ester | 174799-86-1

• 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: 4-(Benzyl-benzyloxycarbonylmethyl-amino)-butyric acid tert-butyl ester
• 英文别名: Tert-butyl 4-[benzyl-(2-oxo-2-phenylmethoxyethyl)amino]butanoate
• CAS: 174799-86-1
• 化学式: C₂₄H₃₁NO₄
• 分子量: 397.514
• InChiKey: OSTUFNVFKUCHFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(Benzyl-benzyloxycarbonylmethyl-amino)-butyric acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 8.0h， 生成 4-[Carboxymethyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-butyric acid tert-butyl ester
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e
• 作为产物：
  描述：

  tert-butyl 4-(((benzyloxy)carbonyl)amino)butanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 magnesium sulfate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -5.0~25.0 ℃ 、413.69 kPa 条件下， 反应 9.0h， 生成 4-(Benzyl-benzyloxycarbonylmethyl-amino)-butyric acid tert-butyl ester
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e