(3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1S)-2-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]cyclohex-2-en-1-yl]azetidin-2-one | 184531-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1S)-2-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]cyclohex-2-en-1-yl]azetidin-2-one
• 英文别名: (3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1S)-2-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidin-2-yl]oxy]cyclohex-2-en-1-yl]azetidin-2-one
• CAS: 184531-16-6
• 化学式: C₂₇H₄₃N₂O₅PSi
• 分子量: 534.708
• InChiKey: BVWZLXZWFMOEMH-MUTWPTQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1S)-2-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]cyclohex-2-en-1-yl]azetidin-2-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以80%的产率得到(3R,4S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(1S,2S,6S)-1-((2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yloxy)-7-oxa-bicyclo[4.1.0]hept-2-yl]-azetidin-2-one
  参考文献：
  名称：

  Highly stereocontrolled synthesis of enantiomeric 4-methoxy trinems via resolution of scalemic enol phosphates

  摘要：

  Stereocontrolled syntheses of 4-methoxy trinem 2 and its enantiomer 3 were achieved using the ester enolate N-trimethylsilylimine approach. The key step was the resolution of racemic enolphosphates derived from ephedrine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00384-9
• 作为产物：
  描述：

  麻黄碱 在 potassium fluoride 、 LiHMDSA 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3R,4S)-3-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1S)-2-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]cyclohex-2-en-1-yl]azetidin-2-one
  参考文献：
  名称：

  Highly stereocontrolled synthesis of enantiomeric 4-methoxy trinems via resolution of scalemic enol phosphates

  摘要：

  Stereocontrolled syntheses of 4-methoxy trinem 2 and its enantiomer 3 were achieved using the ester enolate N-trimethylsilylimine approach. The key step was the resolution of racemic enolphosphates derived from ephedrine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00384-9

文献信息

• Highly stereocontrolled synthesis of enantiomeric 4-methoxy trinems via resolution of scalemic enol phosphates
  作者：Mauro Panunzio、Roberto Camerini、Roberta Pachera、Daniele Donati、Carla Marchioro、Alcide Perboni

  DOI：10.1016/0957-4166(96)00384-9

  日期：1996.10

  Stereocontrolled syntheses of 4-methoxy trinem 2 and its enantiomer 3 were achieved using the ester enolate N-trimethylsilylimine approach. The key step was the resolution of racemic enolphosphates derived from ephedrine. Copyright (C) 1996 Elsevier Science Ltd