dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate | 699020-10-5

• 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: dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate
• 英文别名: L-Aspartic acid, N,N-bis[(phenylmethoxy)carbonyl]-, dimethyl ester；dimethyl (2S)-2-[bis(phenylmethoxycarbonyl)amino]butanedioate
• CAS: 699020-10-5
• 化学式: C₂₂H₂₃NO₈
• 分子量: 429.427
• InChiKey: AQEPBWHMGZMIQI-SFHVURJKSA-N

物化性质

• 沸点：
  538.4±60.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate 在 lithium bromide 作用下， 以 乙腈 为溶剂， 以93%的产率得到Z-Asp-(β-OMe)-OMe
  参考文献：
  名称：

  First Practical Protection of α-Amino Acids as N,N-Benzyloxycarbamoyl Derivatives

  摘要：

  The consecutive treatment of N-Cbz amino protected compounds with LiHMDS and CbzCl provides a practical method for the preparation of N,N-benzyloxycarbamoyl (NN-di-Cbz) derivatives in good yield. When alpha-amino acids are used the protection occurs without racemization. The method is compatible with a wide range of other functional and protecting groups. The procedure is also valid for the synthesis of mixed N,N-carbamoyl derivatives.

  DOI：

  10.1021/jo049759+
• 作为产物：
  描述：

  苄氧甲酸酐 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate
  参考文献：
  名称：

  First Practical Protection of α-Amino Acids as N,N-Benzyloxycarbamoyl Derivatives

  摘要：

  The consecutive treatment of N-Cbz amino protected compounds with LiHMDS and CbzCl provides a practical method for the preparation of N,N-benzyloxycarbamoyl (NN-di-Cbz) derivatives in good yield. When alpha-amino acids are used the protection occurs without racemization. The method is compatible with a wide range of other functional and protecting groups. The procedure is also valid for the synthesis of mixed N,N-carbamoyl derivatives.

  DOI：

  10.1021/jo049759+

文献信息

• First Practical Protection of α-Amino Acids as <i>N,N</i>-Benzyloxycarbamoyl Derivatives
  作者：J. Nicolás Hernández、Víctor S. Martín

  DOI：10.1021/jo049759+

  日期：2004.5.1

  The consecutive treatment of N-Cbz amino protected compounds with LiHMDS and CbzCl provides a practical method for the preparation of N,N-benzyloxycarbamoyl (NN-di-Cbz) derivatives in good yield. When alpha-amino acids are used the protection occurs without racemization. The method is compatible with a wide range of other functional and protecting groups. The procedure is also valid for the synthesis of mixed N,N-carbamoyl derivatives.