tert-butyl (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxypentanoate | 390377-20-5

• 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: tert-butyl (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxypentanoate
• 英文别名: tert-butyl (3R,4S)-4-(dibenzylamino)-3-hydroxypentanoate
• CAS: 390377-20-5
• 化学式: C₂₃H₃₁NO₃
• 分子量: 369.504
• InChiKey: BEVIHYFUZBWMCM-GHTZIAJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxypentanoate 在 三氟乙酸 作用下， 反应 6.0h， 以70%的产率得到(3R,4S)-4-(N,N-dibenzylamino)-3-hydroxypentanoic 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
• 作为产物：
  描述：

  (S)-2-二苄基氨基丙醛 、 (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 以 四氢呋喃 为溶剂， 反应 2.0h， 以54%的产率得到tert-butyl (3R,4S)-4-(N,N-dibenzylamino)-3-hydroxypentanoate
  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