N-[[(2S,5R,6R)-6-[(1R,2S,3S,4R,6S)-3-[(4aR,6R,7R,8R,8aS)-7-hydroxy-8-[(4-methylphenyl)sulfonylamino]spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4,6-bis[(4-methylphenyl)sulfonylamino]cyclohexyl]oxy-5-[(4-methylphenyl)sulfonylamino]oxan-2-yl]methyl]-4-methylbenzenesulfonamide | 119783-70-9

• 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: N-[[(2S,5R,6R)-6-[(1R,2S,3S,4R,6S)-3-[(4aR,6R,7R,8R,8aS)-7-hydroxy-8-[(4-methylphenyl)sulfonylamino]spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4,6-bis[(4-methylphenyl)sulfonylamino]cyclohexyl]oxy-5-[(4-methylphenyl)sulfonylamino]oxan-2-yl]methyl]-4-methylbenzenesulfonamide
• CAS: 119783-70-9
• 化学式: C₅₉H₇₄FN₅O₁₇S₅
• 分子量: 1304.59
• InChiKey: VHHKQSFHMCDBCR-WVSMUZSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  87.0
• 可旋转键数：
  20.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  306.46
• 氢给体数：
  6.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  N-[[(2S,5R,6R)-6-[(1R,2S,3S,4R,6S)-3-[(4aR,6R,7R,8R,8aS)-7-hydroxy-8-[(4-methylphenyl)sulfonylamino]spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4,6-bis[(4-methylphenyl)sulfonylamino]cyclohexyl]oxy-5-[(4-methylphenyl)sulfonylamino]oxan-2-yl]methyl]-4-methylbenzenesulfonamide 在 溶剂黄146 作用下， 反应 0.5h， 以0.52 g的产率得到
  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-5,3',4'-trideoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B 以0.59 g的产率得到N-[[(2S,5R,6R)-6-[(1R,2S,3S,4R,6S)-3-[(4aR,6R,7R,8R,8aS)-7-hydroxy-8-[(4-methylphenyl)sulfonylamino]spiro[4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-2,1'-cyclohexane]-6-yl]oxy-2-fluoro-4,6-bis[(4-methylphenyl)sulfonylamino]cyclohexyl]oxy-5-[(4-methylphenyl)sulfonylamino]oxan-2-yl]methyl]-4-methylbenzenesulfonamide
  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