(αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-N-(4-methoxyphenyl)-azetidin-2-one | 733769-91-0

• 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: (αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-N-(4-methoxyphenyl)-azetidin-2-one
• 英文别名: [(1R)-1-[(2R,3R)-1-(4-methoxyphenyl)-2-(methylsulfonyloxymethyl)-4-oxoazetidin-3-yl]ethyl] acetate
• CAS: 733769-91-0
• 化学式: C₁₆H₂₁NO₇S
• 分子量: 371.411
• InChiKey: UJYKIBBWXNOZGL-ONERCXAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-N-(4-methoxyphenyl)-azetidin-2-one 在 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 水 、 乙腈 为溶剂， 反应 5.5h， 生成 benzyl (αR,6R,7R)-7-(1-acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 2-Isoxacephems

  摘要：

  (alphaR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted beta-lactams. The reduction of methyl [(alphaR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.

  DOI：

  10.1007/s00706-003-0135-9
• 作为产物：
  描述：

  甲基磺酰氯 、 (αR,3R,4R)-3-(1-acetoxyethyl)-4-hydroxymethyl-N-(4-methoxyphenyl)-azetidin-2-one 以 吡啶 为溶剂， 以76%的产率得到(αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-N-(4-methoxyphenyl)-azetidin-2-one
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure 2-Isoxacephems

  摘要：

  (alphaR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted beta-lactams. The reduction of methyl [(alphaR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.

  DOI：

  10.1007/s00706-003-0135-9

文献信息

• Synthesis of Enantiomerically Pure 2-Isoxacephems
  作者：Zsuzsanna S�nta、J�zsef Nagy、L�szl� P�rk�nyi、J�zsef Nyitrai

  DOI：10.1007/s00706-003-0135-9

  日期：2004.6.1

  (alphaR,6R,7R)-7-(1-Acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid and its enantiomer have been prepared. The ring systems were formed from the corresponding enantiomerically pure N-unsubstituted beta-lactams. The reduction of methyl [(alphaR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylate] has been solved via a hemi-acetal. The structure and the configuration of a new stereogenic center in this intermediate was predicted by using 2D NMR technique and unambiguously proven by x-ray.