5,2''-di-O-benzoyl-4'',6''-O-cyclohexylidene-3'4'-dideoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B | 119784-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,2''-di-O-benzoyl-4'',6''-O-cyclohexylidene-3'4'-dideoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B
• 英文别名: [(4aR,6S,7R,8S,8aS)-6-[(1S,2R,3R,4S,6R)-2-benzoyloxy-4,6-bis[(4-methylphenyl)sulfonylamino]-3-[(2R,3R,6S)-3-[(4-methylphenyl)sulfonylamino]-6-[[(4-methylphenyl)sulfonylamino]methyl]oxan-2-yl]oxycyclohexyl]oxy-8-[(4-methylphenyl)sulfonylamino]spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-7-yl] benzoate
• CAS: 119784-01-9
• 化学式: C₇₃H₈₃N₅O₂₀S₅
• 分子量: 1510.81
• InChiKey: XRZLNYFLQAPFPG-SCSCVDSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  103.0
• 可旋转键数：
  24.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  338.83
• 氢给体数：
  5.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  5,2''-di-O-benzoyl-4'',6''-O-cyclohexylidene-3'4'-dideoxy-5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B 生成 4'',6''-O-cyclohexylidene-3'4'-dideoxy-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：

  2''-O-benzoyl-4'',6''-O-cyclohexylidene-3'4'-dideoxy-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 40.0h， 以54%的产率得到5,2''-di-O-benzoyl-4'',6''-O-cyclohexylidene-3'4'-dideoxy-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