N^α-(benzyloxycarbonyl)-O-phosphono>tyrosine benzyl ester | 158817-12-0

• 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^α-(benzyloxycarbonyl)-O-phosphono>tyrosine benzyl ester
• 英文别名: benzyl (2S)-3-[4-[bis[2-[methyl(diphenyl)silyl]ethoxy]phosphoryloxy]phenyl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 158817-12-0
• 化学式: C₅₄H₅₆NO₈PSi₂
• 分子量: 934.185
• InChiKey: YGJSSEHENCALRV-MPLRIKRWSA-N

物化性质

• 沸点：
  897.3±65.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.57
• 重原子数：
  66
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N^α-(benzyloxycarbonyl)-O-phosphono>tyrosine benzyl ester 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 (S)-2-Benzyloxycarbonylamino-3-(4-{hydroxy-[2-(methyl-diphenyl-silanyl)-ethoxy]-phosphoryloxy}-phenyl)-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis

  摘要：

  Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis. The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides. The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.

  DOI：

  10.1021/jo00101a029
• 作为产物：
  描述：

  bis<2-(methyldiphenylsilyl)ethyl> N,N-diisopropylphosphoramidite 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N^α-(benzyloxycarbonyl)-O-phosphono>tyrosine benzyl ester
  参考文献：
  名称：

  Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis

  摘要：

  Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis. The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides. The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.

  DOI：

  10.1021/jo00101a029

文献信息

• Synthesis and Application of Bis-Silylethyl-Derived Phosphate-Protected Fmoc-Phosphotyrosine Derivatives for Peptide Synthesis
  作者：Hann-Guang Chao、Michael S. Bernatowicz、Paul D. Reiss、Gary R. Matsueda

  DOI：10.1021/jo00101a029

  日期：1994.11

  Three Fmoc-phosphotyrosine derivatives with silylethyl-based phosphate protection were synthesized and evaluated for use in peptide synthesis. The stability of these derivatives toward piperidine/DMF (1:4) treatment and their cleavability with TFA solutions were examined. On the basis of these data, the bis[(methyldiphenylsilyl)ethyl]-protected Fmoc-phosphotyrosine derivative or Fmoc-Tyr(PO(3)MDPSE(2))-OH, was shown to be the most suitable candidate for the production of phosphotyrosine peptides. The syntheses of phosphotyrosine peptides including one containing Met and Cys are described.