tert-butyl α-(dimethylphenylsilyl)acetate | 159826-55-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl α-(dimethylphenylsilyl)acetate
• 英文别名: tert-butyl (dimethylphenylsilyl)acetate；t-Butyl (dimethylphenylsilyl)acetate；tert-butyl 2-[dimethyl(phenyl)silyl]acetate
• CAS: 159826-55-8
• 化学式: C₁₄H₂₂O₂Si
• 分子量: 250.413
• InChiKey: JDPYILXUBIWGFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl α-(dimethylphenylsilyl)acetate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 bis<2-(dimethylphenylsilyl)ethyl> N,N-diisopropylphosphoramidite
  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：

  醋酸叔丁酯 、 苯基二甲基氯硅烷 在 lithium diisopropyl amide 作用下， 生成 tert-butyl α-(dimethylphenylsilyl)acetate
  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

• Z-Stereoselective Peterson olefination of ketones
  作者：N. Ya. Grigorieva、O. A. Pinsker、A. V. Buevich、A. M. Moiseenkov

  DOI：10.1007/bf00702395

  日期：1995.3

  A highly-stereoselective method (90 % of theZ-isomer) was developed for the Peterson olefination of ketones with nerylacetone (1) as an example. The method is based on the introduction of a PhS group, which is removed after completion of the reaction, at the ketone C(3) atom.

  以橙花丙酮 (1) 为例，开发了一种高度立体选择性的方法（90% 的 Z-异构体），用于酮与橙花酯 (1) 的 Peterson 烯化。该方法基于在酮 C(3) 原子处引入 PhS 基团，该基团在反应完成后被去除。