(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester | 733769-93-2

• 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: (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester
• CAS: 733769-93-2
• 化学式: C₂₀H₂₅NO₉S
• 分子量: 455.486
• InChiKey: NLJZSZHSEAVHGX-JNKAZWCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  136.51
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (αR,6R,7R)-7-(1-acetoxyethyl)-3-methyl-2-isoxacephem-4-carboxylic acid
  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：

  (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 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester
  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