(2R,5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoic acid | 848617-67-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2R,5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoic acid
• CAS: 848617-67-4
• 化学式: C₂₉H₃₂FNO₃
• 分子量: 461.576
• InChiKey: YUIGRXPXQPQGJM-NAKRPHOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,5S)-5-(dibenzylamino)-2-[(4-fluorophenyl)methyl]-6-methyl-4-oxoheptanoic acid 在 palladium on activated charcoal 硫酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 10.0 ℃ 、344.74 kPa 条件下， 反应 7.0h， 生成 (alphaR)-4-氟-alpha-[(3S)-4-甲基-3-[[(5-甲基-3-异恶唑基)羰基]氨基]-2-氧代戊基]-苯丙酸
  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 、 phosphate buffer 、 Mucor miehei lipase 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 正庚烷 、 水 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 26.83h， 生成 (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

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.