(2S,4S)-2-amino-4-fluoro-5-methoxy-5-oxopentanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-2-amino-4-fluoro-5-methoxy-5-oxopentanoic acid
• 化学式: C₆H₁₀FNO₄
• 分子量: 179.148
• InChiKey: GVLURWYVNWFDFN-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-amino-4-fluoro-5-methoxy-5-oxopentanoic acid 在 ammonium hydroxide 、 Dowex 50W-X₈ 作用下， 生成 (2S,4S)-L-threo-4-fluoroglutamic acid
  参考文献：
  名称：

  Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase

  摘要：

  Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the gamma-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00462-4
• 作为产物：
  描述：

  2-氨基-4-氟-5-甲氧基-5-氧代戊酸 在 ammonium hydroxide 、 porcine kidney aminoacylase 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (2S,4S)-2-amino-4-fluoro-5-methoxy-5-oxopentanoic acid
  参考文献：
  名称：

  Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase

  摘要：

  Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the gamma-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00462-4

文献信息

• Practical synthesis of L-erythro- and L-threo-4-fluoroglutamic acids using aminoacylase
  作者：Yoshitsugu Kokuryo、Takuji Nakatani、Kobee Kobayashi、Yoshinori Tamura、Kenji Kawada、Mitsuaki Ohtani

  DOI：10.1016/s0957-4166(96)00462-4

  日期：1996.12

  Enantiomerically pure L-erythro- and L-threo-4-fluoroglutamic acids 1a and 1b were conveniently prepared. The key steps in this synthesis relied upon separation of diastereomers of N-chloroacetyl-4-fluoroglutamic acid 5-methyl ester 7 by recrystallization and enzymatic resolution of enantiomers of the resulting 7(a+c) and 7(b+d) by aminoacylase. Protection of the gamma-carboxyl group as a methyl ester was found to be crucial for this enzymatic reaction. Copyright (C) 1996 Elsevier Science Ltd.