trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate | 937369-86-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate
• CAS: 937369-86-3
• 化学式: C₃₄H₅₄N₂O₈
• 分子量: 618.811
• InChiKey: ONSATIPPIBUREL-JLEZGDCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate 在 盐酸 、 水 、 ammonium hydroxide 作用下， 以 甲苯 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 4.5h， 以83%的产率得到trans-4-aminocyclohexyl (1S,2R,3S,4S,6R,7R,8R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate
  参考文献：
  名称：

  Process Development for A Novel Pleuromutilin-Derived Antibiotic

  摘要：

  A scalable synthesis of a novel pleuromutilin-based antibiotic is reported. The synthesis features the scale-up of an interesting skeletal rearrangement of the pleuromutilin core and isolation. of a highly purified product despite starting with relatively impure pleuromutilin. The use of Design of Experiment (DoE) and Principal Component Analysis (PCA) tools to achieve these goals is also discussed. Furthermore, the novel coupling of a carbamate and N-acyl-imidazole to produce the imidodicarbonate portion of the target molecule is described.

  DOI：

  10.1021/op900104g
• 作为产物：
  描述：

  (3R,3aS,4R,5R,7S,9R,9aR,12R)-3-methoxy-4,7,9,12-tetramethyl-8-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl carbamate 、 (1r,4r)-4-((tert-butoxycarbonyl)amino)cyclohexyl 1H-imidazole-1-carboxylate 在 sodium tert-pentoxide 、 水 、 柠檬酸 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以90%的产率得到trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl (1R,2R,4S,6R,7R,9R)-4-ethenyl-2,4,7,14-tetramethyl-9-(methyloxy)-3-oxotricyclo[5.4.3.0(1,8)]tetradec-6-yl imidodicarbonate
  参考文献：
  名称：

  Process Development for A Novel Pleuromutilin-Derived Antibiotic

  摘要：

  A scalable synthesis of a novel pleuromutilin-based antibiotic is reported. The synthesis features the scale-up of an interesting skeletal rearrangement of the pleuromutilin core and isolation. of a highly purified product despite starting with relatively impure pleuromutilin. The use of Design of Experiment (DoE) and Principal Component Analysis (PCA) tools to achieve these goals is also discussed. Furthermore, the novel coupling of a carbamate and N-acyl-imidazole to produce the imidodicarbonate portion of the target molecule is described.

  DOI：

  10.1021/op900104g