ethyl (2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(4-phenylmethoxyphenyl)propanoate | 481072-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(4-phenylmethoxyphenyl)propanoate
• CAS: 481072-39-3
• 化学式: C₂₄H₃₄O₄Si
• 分子量: 414.617
• InChiKey: DYLTXPKNKUXVHW-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(4-phenylmethoxyphenyl)propanoate 在 palladium on activated charcoal 三乙基硅烷 、 bismuth(III) bromide 、 氢气 、 caesium carbonate 、 乙醛 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~25.0 ℃ 、344.74 kPa 条件下， 生成 ethyl (2S)-2-ethoxy-3-[4-(1-oxo-1-phenylmethoxypropan-2-yl)oxyphenyl]propanoate
  参考文献：
  名称：

  Synthesis of a Peroxime Proliferator Activated Receptor (PPAR) α/γ Agonist via Stereocontrolled Williamson Ether Synthesis and Stereospecific S_N2 Reaction of S-2-Chloro Propionic Acid with Phenoxides

  摘要：

  The stereospecific synthesis of the PPAR alpha/gamma agonist I was accomplished via ethylation of the optically pure tribydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30 degrees C), order of addition, and solvent (DMF). The key diastereospecific S(N)2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na-0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described.

  DOI：

  10.1021/jo050268e
• 作为产物：
  描述：

  (S)-3-(4-苄氧基苯基)-2-羟基丙酸 在 咪唑 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ethyl (2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-(4-phenylmethoxyphenyl)propanoate
  参考文献：
  名称：

  Synthesis of a Peroxime Proliferator Activated Receptor (PPAR) α/γ Agonist via Stereocontrolled Williamson Ether Synthesis and Stereospecific S_N2 Reaction of S-2-Chloro Propionic Acid with Phenoxides

  摘要：

  The stereospecific synthesis of the PPAR alpha/gamma agonist I was accomplished via ethylation of the optically pure tribydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30 degrees C), order of addition, and solvent (DMF). The key diastereospecific S(N)2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na-0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described.

  DOI：

  10.1021/jo050268e