(2R,3S)-N-benzyl-3,4-dibenzyloxy-2-butylamine | 175730-15-1

• 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: (2R,3S)-N-benzyl-3,4-dibenzyloxy-2-butylamine
• 英文别名: (2R,3S)-N-benzyl-3,4-bis(benzyloxy)butan-2-amine；(2R,3S)-N-benzyl-3,4-bis(phenylmethoxy)butan-2-amine
• CAS: 175730-15-1
• 化学式: C₂₅H₂₉NO₂
• 分子量: 375.511
• InChiKey: DFLQWVUGPZYMQH-PXDATVDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲酸甲酯 、 (2R,3S)-N-benzyl-3,4-dibenzyloxy-2-butylamine 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(2R,3S)-N-benzyl-3,4-dibenzyloxy-N-methoxycarbonyl-2-butylamine
  参考文献：
  名称：

  Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source

  摘要：

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.

  DOI：

  10.1016/0957-4166(96)00037-7
• 作为产物：
  描述：

  (+)-(R)-2,3-bis(benzyloxy)propanal 在 magnesium sulfate 作用下， 以 乙醚 、 二丁醚 为溶剂， 反应 18.0h， 生成 (2R,3S)-N-benzyl-3,4-dibenzyloxy-2-butylamine
  参考文献：
  名称：

  Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source

  摘要：

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.

  DOI：

  10.1016/0957-4166(96)00037-7

文献信息

• Diastereoselective reduction of ketimines derived from (R)-3,4-dihydroxybutan-2-one: an alternative route to key intermediates for the synthesis of anticancer agent ES-285
  作者：Ana C. Allepuz、Ramón Badorrey、María D. Díaz-de-Villegas、José A. Gálvez

  DOI：10.1016/j.tetasy.2010.02.012

  日期：2010.3

  A simple and convenient procedure for the diastereoselective reduction of imines derived from (R)-3,4-dihydroxybutan-2-one is described. The use of sodium borohydride as a reducing agent in the reactions with pre-synthesised imines gave aminodiol derivatives with the appropriate stereochemistry for use as intermediates in the synthesis of anticancer agent ES-285. The aminodiols were isolated in ca. 62% yield. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of α-hydroxy-β-amino acids using D-glyceraldehyde as the homochiral source
  作者：Carlos Cativiela、Maria D. Diaz-de-Villegas、JoséA. Gálvez

  DOI：10.1016/0957-4166(96)00037-7

  日期：1996.2

  A systematic study of the diastereoselective addition of methyl organometallic compounds to the benzyl imine derived from conveniently protected D-glyceraldehyde in order to develop a new approach to enantiomerically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesium bromide addition afforded the corresponding adduct, which can be further elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.