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 succinic acid salt | 1070293-46-7

• 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-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 succinic acid salt
• CAS: 1070293-46-7
• 化学式: C₄H₆O₄*C₂₈H₄₄N₂O₆
• 分子量: 622.756
• InChiKey: OCQUXYWNOUVDAX-NOQQIWFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  202.55
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  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 、 丁二酸 以 水 、 异丙醇 为溶剂， 以92%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 succinic acid salt
  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