(4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[di((114C)methyl)carbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate | 1206708-70-4

• 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: (4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[di((114C)methyl)carbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 1206708-70-4
• 化学式: C₃₂H₃₅N₅O₁₁S
• 分子量: 701.701
• InChiKey: PJGGEFUAFDAJJT-CJVHFABHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  49
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  234
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[di((114C)methyl)carbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (4R,5S,6S)-3-[(3S,5S)-5-[di((114C)methyl)carbamoyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of labeled meropenem for the analysis of M. tuberculosis transpeptidases

  摘要：

  A concise synthesis of C-14 labeled meropenem prepared from C-14 dimethylamine hydrochloride is described. Using a similar reaction sequence, the meropenem nucleus was also attached to biotin providing a probe for protein interaction studies. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.10.124
• 作为产物：
  描述：

  (4-nitrophenyl)methyl (2S,4S)-2-[di((114C)methyl)carbamoyl]-4-sulfanylpyrrolidine-1-carboxylate 、 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以48%的产率得到(4-nitrophenyl)methyl (4R,5S,6S)-3-[(3S,5S)-5-[di((114C)methyl)carbamoyl]-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis of labeled meropenem for the analysis of M. tuberculosis transpeptidases

  摘要：

  A concise synthesis of C-14 labeled meropenem prepared from C-14 dimethylamine hydrochloride is described. Using a similar reaction sequence, the meropenem nucleus was also attached to biotin providing a probe for protein interaction studies. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.10.124

文献信息

• Synthesis of labeled meropenem for the analysis of M. tuberculosis transpeptidases
  作者：David B. Kastrinsky、Clifton E. Barry

  DOI：10.1016/j.tetlet.2009.10.124

  日期：2010.1

  A concise synthesis of C-14 labeled meropenem prepared from C-14 dimethylamine hydrochloride is described. Using a similar reaction sequence, the meropenem nucleus was also attached to biotin providing a probe for protein interaction studies. Published by Elsevier Ltd.