Benzyl (S)-2-<-2-phenylethyl>phosphoryl>oxy>-3-methylbutanoate | 153465-22-6

• 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: Benzyl (S)-2-<-2-phenylethyl>phosphoryl>oxy>-3-methylbutanoate
• 英文别名: benzyl (2S)-2-[methoxy-[(1R)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]oxy-3-methylbutanoate
• CAS: 153465-22-6
• 化学式: C₂₉H₃₄NO₇P
• 分子量: 539.565
• InChiKey: LLGRESGWKOSYQU-DSJTWFBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzyl (S)-2-<-2-phenylethyl>phosphoryl>oxy>-3-methylbutanoate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以52%的产率得到Benzyl (S)-2-<<<(R)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl>hydroxyphosphoryl>oxy>-3-methylbutanoate
  参考文献：
  名称：

  (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters

  摘要：

  A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.

  DOI：

  10.1021/jo00121a045
• 作为产物：
  描述：

  (R)-<1-<(Benzyloxycarbonyl)amino>-2-phenylethyl>phosphonous acid 在 4-二甲氨基吡啶 、 sodium periodate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 Benzyl (S)-2-<-2-phenylethyl>phosphoryl>oxy>-3-methylbutanoate
  参考文献：
  名称：

  (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters

  摘要：

  A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.

  DOI：

  10.1021/jo00121a045

文献信息

• (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters
  作者：Jean-Marc Campagne、Jacques Coste、Patrick Jouin

  DOI：10.1021/jo00121a045

  日期：1995.8

  A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.