[tert-butyl(dimethyl)silyl] (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate | 134150-54-2

• 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: [tert-butyl(dimethyl)silyl] (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate
• CAS: 134150-54-2
• 化学式: C₃₀H₃₅NO₅Si
• 分子量: 517.697
• InChiKey: OJNNJUUGBJYDMO-MHZLTWQESA-N

物化性质

• 沸点：
  644.8±55.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [tert-butyl(dimethyl)silyl] (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 水 、 乙腈 为溶剂， 反应 3.17h， 生成
  参考文献：
  名称：

  Development of Non-Peptide Ligands of Growth Factor Receptor-Bound Protein 2-Src Homology 2 Domain Using Molecular Modeling and NMR Spectroscopy

  摘要：

  We report a novel series of non-peptide ligands that inhibit the growth factor receptor-bound protein 2 (Grb2)-Src homology 2 (SH2) domain binding, designed using a combined computational and NMR-driven approach. We have identified a new lead compound, in (IC50 = 56 mu M), which is cytotoxic in HER2-positive breast cancer cells and disrupts the interaction between HER2 and Grb2. Thus, In can be used as a scaffold for the development of efficient Grb2-SH2 domain binding inhibitors.

  DOI：

  10.1021/jm101478n
• 作为产物：
  描述：

  L-酪氨酸 在 N-甲基吗啉 、 碳酸氢钠 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 20.25h， 生成 [tert-butyl(dimethyl)silyl] (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate
  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

• A general and convenient synthesis of novel phosphotyrosine mimetics
  作者：Anna Katrin Szardenings、Mikhail F. Gordeev、Dinesh V. Patel

  DOI：10.1016/0040-4039(96)00666-1

  日期：1996.5

  A simple and general procedure for preparation of various phosphotyrosine mimetics from the corresponding phenolic precursors is described. In situ silylation of phenol acids followed by treatment with Et3N/CBr4/HP(O)(OEt)2 provides diethyl phosphate intermediates (36–96%), which can be cleanly deprotected in quantitative yields upon treatment with BSTFA/TMSI to afford novel phosphotyrosine mimetics

  描述了一种由相应的酚类前体制备各种磷酸酪氨酸模拟物的简单通用方法。酚酸的原位甲硅烷基化，然后用Et 3 N / CBr 4 / HP（O）（OEt）2处理可提供磷酸二乙酯中间体（36–96％），在用BSTFA / TMSI处理后可以定量地将其干净地脱保护提供新型的磷酸酪氨酸模拟物。
• Phosphopeptide Prodrug Bearing an <i>S</i>-Acyl-2-thioethyl Enzyme-Labile Phosphate Protection
  作者：Christophe Mathé,、Christian Périgaud、Gilles Gosselin、Jean-Louis Imbach

  DOI：10.1021/jo980437d

  日期：1998.11.1