(S)-3-Phenyl-2-prop-2-ynyloxycarbonylamino-propionic acid pentafluorophenyl ester | 439912-39-7

• 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: (S)-3-Phenyl-2-prop-2-ynyloxycarbonylamino-propionic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2S)-3-phenyl-2-(prop-2-ynoxycarbonylamino)propanoate
• CAS: 439912-39-7
• 化学式: C₁₉H₁₂F₅NO₄
• 分子量: 413.301
• InChiKey: OSZIIXGBIRUFOZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 (S)-3-Phenyl-2-prop-2-ynyloxycarbonylamino-propionic acid pentafluorophenyl ester 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.75h， 以89%的产率得到Poc-Phe-Ala-OH
  参考文献：
  名称：

  Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis

  摘要：

  Propargyl pentafluorophenyl carbonate was synthesised in quantitative yield by the reaction of propargyl chloroformate and pentafluorophenol. All the N-propargyloxycarbonyl (N-Poc) amino acids were obtained in good yield. The use of Poc-OPfp in peptide synthesis has been explored. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00287-3
• 作为产物：
  描述：

  L-苯丙氨酸 、 propargyl pentafluorophenyl carbonate 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到(S)-3-Phenyl-2-prop-2-ynyloxycarbonylamino-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate

  摘要：

  A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.

  DOI：

  10.1021/ol060494q

文献信息

• Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis
  作者：Ramakrishna G Bhat、Erwan Kérourédan、Emmanuel Porhiel、Srinivasan Chandrasekaran

  DOI：10.1016/s0040-4039(02)00287-3

  日期：2002.3

  Propargyl pentafluorophenyl carbonate was synthesised in quantitative yield by the reaction of propargyl chloroformate and pentafluorophenol. All the N-propargyloxycarbonyl (N-Poc) amino acids were obtained in good yield. The use of Poc-OPfp in peptide synthesis has been explored. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate
  作者：Ramapanicker Ramesh、Sakthidevi Rajasekaran、Rohit Gupta、Srinivasan Chandrasekaran

  DOI：10.1021/ol060494q

  日期：2006.4.1

  A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.