2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B | 144487-82-1

• 分子结构分类: 有机化合物
• 英文名称: 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
• CAS: 144487-82-1
• 化学式: C₆₁H₇₇N₅O₂₀S₅
• 分子量: 1360.63
• InChiKey: GLNBLHOSQPGJAG-OOFOVOHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  91.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  352.99
• 氢给体数：
  7.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B 、 苯甲酸 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 various solvent(s) 为溶剂， 反应 1.5h， 以69%的产率得到2''-O-acetyl-5-O-benzoyl-4'',6''-O-cyclohexylidene-3'-deoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin 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：

  环己酮二甲缩酮 在 吡啶 、 对甲苯磺酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2''-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin 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