(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{(2R,3R)-2-[(4-nitro-benzyloxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester | 194995-41-0

• 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: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{(2R,3R)-2-[(4-nitro-benzyloxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester
• CAS: 194995-41-0
• 化学式: C₂₇H₃₃N₃O₁₂S
• 分子量: 623.638
• InChiKey: BAYJVWGQGXIJDB-OFFWLINVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  193.07
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{(2R,3R)-2-[(4-nitro-benzyloxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  Mono and bis double ester prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Mono and bis double ester prodrugs of aminomethyl THF 1 beta-methylcarbapenems 1 were Mono double ester derivatives (2, 4 and 7) did not demonstrate significantly improved oral activity due to the presence of the charged species. However, bis double ester derivatives (3 and 5) demonstrated enhanced oral activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00305-3
• 作为产物：
  描述：

  4-nitrobenzyl 4-nitrophenyl carbonate 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-{(2R,3R)-2-[(4-nitro-benzyloxycarbonylamino)-methyl]-tetrahydro-furan-3-ylsulfanyl}-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid ethoxycarbonyloxymethyl ester
  参考文献：
  名称：

  Mono and bis double ester prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Mono and bis double ester prodrugs of aminomethyl THF 1 beta-methylcarbapenems 1 were Mono double ester derivatives (2, 4 and 7) did not demonstrate significantly improved oral activity due to the presence of the charged species. However, bis double ester derivatives (3 and 5) demonstrated enhanced oral activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00305-3