(αR,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid | 733769-99-8

• 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,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid
• 英文别名: (2S,3R)-3-[(1R)-1-hydroxyethyl]-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid
• CAS: 733769-99-8
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: WWINMNUUOFPBIH-GGVZMXCHSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  591.3±45.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (αR,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid 在 吡啶 、 ammonium cerium(IV) nitrate 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry

  摘要：

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.034
• 作为产物：
  描述：

  methyl [(αR,2S,3R)-3-(1-acetoxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate] 在 盐酸 作用下， 反应 20.0h， 以77%的产率得到(αR,2S,3R)-3-(1-hydroxyethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-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

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.
• Synthesis of thienamycin-like 2-iso-oxacephems with optional stereochemistry
  作者：Zsuzsanna Sánta、József Nagy、József Nyitrai

  DOI：10.1016/j.tetasy.2006.11.034

  日期：2006.11

  All four traps-stereoisomers of 7-(1-hydroxyethyl)-2-iso-oxacephem-4-carboxylic acids, which are the 2-iso-oxacephem analogues of Thienamycin, have been synthesized. (alpha R,6R,7R)- and (alpha S,6S,7S)-7-(1-hydroxyethyl)-3-methyl-2-iso-oxacephem-4-carboxylic acids have been prepared starting from L- and D-threonine, the configuration at the a-position was inverted by using Mitsunobu reactions providing the (alpha S,6R,7R)- and (alpha R,6S,7S)-diastereomers of the compounds above. A synthetic route to the cis-annelated analogues was also worked out. (c) 2006 Elsevier Ltd. All rights reserved.