ethyl (5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoate | 848617-65-2

• 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: ethyl (5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoate
• CAS: 848617-65-2
• 化学式: C₃₁H₃₆FNO₃
• 分子量: 489.63
• InChiKey: GARKNNSLCADNNU-MILIPEGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoate 在 phosphate buffer 、 Mucor miehei lipase 作用下， 以 正庚烷 、 水 为溶剂， 以45%的产率得到(2R,5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of ketomethylene tripeptide isosteres

  摘要：

  A chemoenzymatic method is described for the synthesis of a desired ketomethylene tripeptide isostere. The key step is an enzymatic hydrolysis, which removes the C-terminal ester-protecting group under mild conditions without epimerizing the existing stereogenic center and produces the desired stereoisomer in high enantiomeric excess (98% de, 97% ee). The method is short with overall 15-20% yields after seven synthetic steps from readily available starting materials being obtained. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.11.092
• 作为产物：
  描述：

  (S)-benzyl 2-(dibenzylamino)-3-methylbutanoate 在 palladium on activated charcoal 正丁基锂 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 26.83h， 生成 ethyl (5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoate
  参考文献：
  名称：

  Chemoenzymatic synthesis of ketomethylene tripeptide isosteres

  摘要：

  A chemoenzymatic method is described for the synthesis of a desired ketomethylene tripeptide isostere. The key step is an enzymatic hydrolysis, which removes the C-terminal ester-protecting group under mild conditions without epimerizing the existing stereogenic center and produces the desired stereoisomer in high enantiomeric excess (98% de, 97% ee). The method is short with overall 15-20% yields after seven synthetic steps from readily available starting materials being obtained. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.11.092

文献信息

• Chemoenzymatic synthesis of ketomethylene tripeptide isosteres
  作者：Junhua Tao、Shanghui Hu、Qingping Tian、Naresh Nayyar、Srin Babu

  DOI：10.1016/j.tetasy.2004.11.092

  日期：2005.2

  A chemoenzymatic method is described for the synthesis of a desired ketomethylene tripeptide isostere. The key step is an enzymatic hydrolysis, which removes the C-terminal ester-protecting group under mild conditions without epimerizing the existing stereogenic center and produces the desired stereoisomer in high enantiomeric excess (98% de, 97% ee). The method is short with overall 15-20% yields after seven synthetic steps from readily available starting materials being obtained. (C) 2005 Published by Elsevier Ltd.