(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,2R,6R)-1-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]-7-oxabicyclo[4.1.0]heptan-2-yl]azetidin-2-one | 184531-17-7

• 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: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,2R,6R)-1-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]-7-oxabicyclo[4.1.0]heptan-2-yl]azetidin-2-one
• 英文别名: (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,2R,6R)-1-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2λ5-oxazaphospholidin-2-yl]oxy]-7-oxabicyclo[4.1.0]heptan-2-yl]azetidin-2-one
• CAS: 184531-17-7
• 化学式: C₂₇H₄₃N₂O₆PSi
• 分子量: 550.707
• InChiKey: BGZIFIIAKCSNDX-QUMDQODWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R)-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	184531-15-5	C27H43N2O5PSi	534.708
  ——	(3S,4R)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R)-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	184531-13-3	C33H57N2O5PSi2	648.971

反应信息

• 作为反应物：
  描述：

  甲醇 、 (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,2R,6R)-1-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]-7-oxabicyclo[4.1.0]heptan-2-yl]azetidin-2-one 反应 5.0h， 以70%的产率得到(3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-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 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (3S,4R)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-[(1R,2R,6R)-1-[[(2S,4S,5R)-3,4-dimethyl-2-oxo-5-phenyl-1,3,2lambda5-oxazaphospholidin-2-yl]oxy]-7-oxabicyclo[4.1.0]heptan-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

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