(+/-)-methyl N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate | 714222-55-6

• 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 N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate
• CAS: 714222-55-6
• 化学式: C₃₀H₄₅NO₆Si₂
• 分子量: 571.861
• InChiKey: WUDUCPGSFHICDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.5h， 生成 (+/-)-(Z)-α-(2'-fluoro)vinyl-3'',4''-dihydroxyphenylalanine hydrochloride
  参考文献：
  名称：

  Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch:  Potential PLP Enzyme Inactivators

  摘要：

  Protected alpha-formyl amino acids, themselves available from the corresponding a-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinyistannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.

  DOI：

  10.1021/ol049422u
• 作为产物：
  描述：

  Methyl N-benzoyl-2-vinyl-3',4'-bis<(tert-butyldimethylsilyl)oxy>phenylalaninate 在 臭氧 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(+/-)-methyl N-benzoyl-α-formyl-3',4'-bis(tert-butyldimethylsilyloxy)phenylalaninate
  参考文献：
  名称：

  Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch:  Potential PLP Enzyme Inactivators

  摘要：

  Protected alpha-formyl amino acids, themselves available from the corresponding a-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinyistannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.

  DOI：

  10.1021/ol049422u