methyl (2S)-2-fluoro-2-(toluene-4-sulfonyloxymethyl)-3-phenylpropanoate | 1013088-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S)-2-fluoro-2-(toluene-4-sulfonyloxymethyl)-3-phenylpropanoate
• 英文别名: methyl (2S)-2-benzyl-2-fluoro-3-(4-methylphenyl)sulfonyloxypropanoate
• CAS: 1013088-77-1
• 化学式: C₁₈H₁₉FO₅S
• 分子量: 366.41
• InChiKey: ZUSIKHJWBMSUDW-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-fluoro-2-(toluene-4-sulfonyloxymethyl)-3-phenylpropanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以77%的产率得到methyl (2S)-2-fluoro-2-azidomethyl-3-phenylpropanoate
  参考文献：
  名称：

  Enantioselective Synthesis of α-Fluorinated β²-Amino Acids

  摘要：

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.

  DOI：

  10.1021/ol703045z
• 作为产物：
  描述：

  methyl (2S)-2-hydroxymethyl-2-fluoro-3-phenylpropanoate 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到methyl (2S)-2-fluoro-2-(toluene-4-sulfonyloxymethyl)-3-phenylpropanoate
  参考文献：
  名称：

  Enantioselective Synthesis of α-Fluorinated β²-Amino Acids

  摘要：

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.

  DOI：

  10.1021/ol703045z

文献信息

• Enantioselective Synthesis of α-Fluorinated β²-Amino Acids
  作者：Michael K. Edmonds、Florian H. M. Graichen、James Gardiner、Andrew D. Abell

  DOI：10.1021/ol703045z

  日期：2008.3.1

  A methodology for the enantioselective synthesis of a-fluorinated beta(2)-amino acids has been developed from readily available carboxylic acids 3. Conversion to the Evan's oxazolidinone followed by enantioselective-fluorination and alkylation gave 7 in high diastereomeric excess (> 95%). Subsequent removal of the oxazolidinone and amination at the Bn-protected hydroxyl center gave optically active alpha-fluorinated beta(2)-amino acids.