(4R,5S,6S)-3-[(3R,5S)-5-(aminomethyl)oxolan-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

• 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)-3-[(3R,5S)-5-(aminomethyl)oxolan-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 化学式: C₁₅H₂₂N₂O₅S
• 分子量: 342.416
• InChiKey: DAUDNOHUBCAECI-RRDOJEEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-3-[(3R,5S)-5-(aminomethyl)oxolan-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 、 (S)-2-(4-Nitro-benzyloxycarbonylamino)-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 以 1,4-二氧六环 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Peptidic prodrugs of novel aminomethyl-THF 1β-methylcarbapenems

  摘要：

  Peptidic prodrugs of the five most active aminomethyl-THF 1 beta-methylcarbapenems were synthesized. Of these, only L-amino acid derivatives from la demonstrated an improved oral activity. These results indicate that the L-amino acid derivatives from la are orally absorbed most likely through the dipeptide and tripeptide transport mechanism. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00281-3
• 作为产物：
  描述：

  杂氮双环磷酸酯 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 (4R,5S,6S)-3-[(3R,5S)-5-(aminomethyl)oxolan-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 and structure-activity relationships of novel THF 1β-methylcarbapenems

  摘要：

  A series of twelve highly active aminomethyl-THF 1 beta-methylcarbapenems 3a-1 were synthesized. Of these, carbapenems 3a-f demonstrated a spectrum of antimicrobial activity comparable to those of imipenem and meropenem with the exception of only moderate anti-pseudomonal activity. Most importantly, they demonstrated moderate intrinsic oral activity against an E. coli infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00282-5