(3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid | 390377-68-1

• 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: (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
• 英文别名: (3R,4S)-4-(dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
• CAS: 390377-68-1
• 化学式: C₂₅H₂₇NO₃
• 分子量: 389.494
• InChiKey: FIAJCVPNNFSBMD-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 26.0h， 以97%的产率得到(3R,4S)-4-氨基-3-羟基-5-苯基戊酸
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

  摘要：

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00804-3
• 作为产物：
  描述：

  苯丙醛,a-[二(苯基甲基)氨基]-,(S)- 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxy-5-phenylpentanoic acid
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes

  摘要：

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00804-3

文献信息

• Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes
  作者：José M Andrés、Rafael Pedrosa、Alberto Pérez、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4020(01)00804-3

  日期：2001.10

  N,N-Dibenzylamino aldehydes 1 react with Reformatsky's reagent leading to anti-gamma -dibenzylamino-beta -hydroxy esters 2 as the major stereoisomers. Treatment of 2 with TFA followed by hydrogenolysis on Pearlman's catalyst yields the corresponding-gamma -amino-beta -hydroxy acids 10. Contrarily, some N-butoxycarbonyl (Boc) amino aldehydes lead to syn-gamma -tert-butoxycarbonylamino-beta -hydroxy esters as the major product. (C) 2001 Elsevier Science Ltd. All rights reserved.