1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3'-dideoxy-5,5-difluorokanamycin B | 142859-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3'-dideoxy-5,5-difluorokanamycin B
• CAS: 142859-95-8
• 化学式: C₅₈H₆₅F₂N₅O₁₈
• 分子量: 1158.17
• InChiKey: GQCGEFBJVYAXNO-RTNBEJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  83.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  309.49
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3'-dideoxy-5,5-difluorokanamycin B 在 钯 氢气 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 以99%的产率得到5,3'-dideoxy-5,5-difluorokanamycin B
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B in its analogs. Study on structure-toxicity relationships

  摘要：

  5-Deoxy-5-fluoro- (1), 5,3'-dideoxy-5-fluoro- (2), and 5,3',4'-trideoxy-5-fluoro-kanamycin B (3) have been prepared by treatment of 5-epihydroxyl precursors (prepared by the Mitsunobu reaction) with DAST as the key step. 5,3'-Dideoxy-5,5-difluoro- (26) and 5,3',4'-trideoxy-5,5-difluoro-kanamycin B (27) were also prepared by treatment of the corresponding 5-oxo derivatives with DAST. These 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives showed markedly decreased toxicity as compared with the parent compounds.

  DOI：

  10.1016/0008-6215(92)80060-e
• 作为产物：
  描述：

  4',2'',4'',6''-tetra-O-acetyl-1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B 在 3 A molecular sieve 、 sodium methylate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 80.67h， 生成 1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3'-dideoxy-5,5-difluorokanamycin B
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B in its analogs. Study on structure-toxicity relationships

  摘要：

  5-Deoxy-5-fluoro- (1), 5,3'-dideoxy-5-fluoro- (2), and 5,3',4'-trideoxy-5-fluoro-kanamycin B (3) have been prepared by treatment of 5-epihydroxyl precursors (prepared by the Mitsunobu reaction) with DAST as the key step. 5,3'-Dideoxy-5,5-difluoro- (26) and 5,3',4'-trideoxy-5,5-difluoro-kanamycin B (27) were also prepared by treatment of the corresponding 5-oxo derivatives with DAST. These 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives showed markedly decreased toxicity as compared with the parent compounds.

  DOI：

  10.1016/0008-6215(92)80060-e