N-(N-benzyloxycarbonylglycyl)-4-hydroxy-L-proline methyl ester | 516526-78-6

• 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: N-(N-benzyloxycarbonylglycyl)-4-hydroxy-L-proline methyl ester
• CAS: 516526-78-6
• 化学式: C₁₆H₂₀N₂O₆
• 分子量: 336.345
• InChiKey: VTYMBLDLXOKHCJ-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.05
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(N-benzyloxycarbonylglycyl)-4-hydroxy-L-proline methyl ester 在 sodium hydroxide 、 铬酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.67h， 生成 N-(N-benzyloxycarbonylglycyl)-4-cis-(benzyloxycarbonylmethyl)acetamido-L-proline methyl ester
  参考文献：
  名称：

  摘要：

  An amination of 4-oxoproline derivatives with glycine methyl or benzyl ester and sodium cyanoborohydride led to the mixtures of corresponding diastereomeric 4-cis- and 4-trans-glycinoproline derivatives. We found that the ratio of diastereomers mainly depends on the structure of 4-oxoproline ester groups and, to a lesser extent, on the structure of N-acyl substituents. The best results were achieved with tert-butyl ester group; it ensured good yields of the amination products and the greatest prevalence of 4-cis-isomers. The structure of ester group in glycine molecule only scarcely affected the resulting ratio of N-(N-benzvloxycarbonylglycyl)-4-glycinoprolines.

  DOI：

  10.1023/a:1021237314299
• 作为产物：
  描述：

  Z-甘氨酸 N-琥珀酰亚胺酯 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.17h， 生成 N-(N-benzyloxycarbonylglycyl)-4-hydroxy-L-proline methyl ester
  参考文献：
  名称：

  摘要：

  An amination of 4-oxoproline derivatives with glycine methyl or benzyl ester and sodium cyanoborohydride led to the mixtures of corresponding diastereomeric 4-cis- and 4-trans-glycinoproline derivatives. We found that the ratio of diastereomers mainly depends on the structure of 4-oxoproline ester groups and, to a lesser extent, on the structure of N-acyl substituents. The best results were achieved with tert-butyl ester group; it ensured good yields of the amination products and the greatest prevalence of 4-cis-isomers. The structure of ester group in glycine molecule only scarcely affected the resulting ratio of N-(N-benzvloxycarbonylglycyl)-4-glycinoprolines.

  DOI：

  10.1023/a:1021237314299

文献信息

• Synthesis of a C₃-Symmetric Nanoscale Molecular Platform Based on Marine Cyclopeptides
  作者：Gebhard Haberhauer

  DOI：10.1055/s-2004-822906

  日期：——

  Efficient synthesis of a conformationally preorganized, C3-symmetric molecular platform is reported. The rigid scaffold is based on the structure of marine cyclopeptides and presents three functional groups pointing in the same direction. The bicyclic imidazole building blocks were synthesized in seven steps from trans-4-hydroxy-(S)-proline.

  报道了一种高效合成构象预组织的三重对称分子平台的方法。该刚性骨架基于海洋环肽的结构，呈现出三个指向相同方向的功能团。双环咪唑构建模块从反式4-羟基-(S)-脯氨酸出发，经过七步合成得到。