dimethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonyl-phenylmethoxycarbonylamino]butanedioate | 1187581-94-7

• 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-[(2-methylpropan-2-yl)oxycarbonyl-phenylmethoxycarbonylamino]butanedioate
• CAS: 1187581-94-7
• 化学式: C₁₉H₂₅NO₈
• 分子量: 395.409
• InChiKey: HWIUMKWWSSZSBN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-[(2-methylpropan-2-yl)oxycarbonyl-phenylmethoxycarbonylamino]butanedioate 在 bismuth(III) bromide 、 水 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以78%的产率得到Z-Asp-(β-OMe)-OMe
  参考文献：
  名称：

  Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile

  摘要：

  Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other Protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.104

文献信息

• Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile
  作者：Jianlong Zheng、Biaolin Yin、Wenming Huang、Xiaopeng Li、Hequan Yao、Zhaogui Liu、Jiancun Zhang、Sheng Jiang

  DOI：10.1016/j.tetlet.2009.06.104

  日期：2009.9

  Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other Protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst. (C) 2009 Elsevier Ltd. All rights reserved.