3',4',2'',4'',6''-penta-O-acetyl-5-deoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B | 119793-47-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',4',2'',4'',6''-penta-O-acetyl-5-deoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B
• 英文别名: [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-[(1S,2S,3R,4S,6R)-3-[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-3-[(4-methylphenyl)sulfonylamino]-6-[[(4-methylphenyl)sulfonylamino]methyl]oxan-2-yl]oxy-2-fluoro-4,6-bis[(4-methylphenyl)sulfonylamino]cyclohexyl]oxy-4-[(4-methylphenyl)sulfonylamino]oxan-2-yl]methyl acetate
• CAS: 119793-47-4
• 化学式: C₆₃H₇₆FN₅O₂₄S₅
• 分子量: 1466.64
• InChiKey: FJUBWBFOONVQCQ-OUYXERTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  98.0
• 可旋转键数：
  26.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  399.27
• 氢给体数：
  5.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  3',4',2'',4'',6''-penta-O-acetyl-5-deoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B 在 氨 、 sodium 作用下， 反应 0.08h， 生成 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-((2R,3R,4R,5R,6R)-4,5-diacetoxy-3-amino-6-aminomethyl-tetrahydro-pyran-2-yloxy)-2-fluoro-cyclohexyloxy]-tetrahydro-pyran-3-yl ester
  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：

  5-epi-1,3,2',6',3''-penta-N-tosylkanamycin B 在 吡啶 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3',4',2'',4'',6''-penta-O-acetyl-5-deoxy-5-fluoro-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

文献信息

• UMEHDZAVA, XAMAO;TOSIDZAVA, DZYUNO;TSUTIYA, OSAMU;SITAGAKU, TEHTSUO;FURUT+
  作者：UMEHDZAVA, XAMAO、TOSIDZAVA, DZYUNO、TSUTIYA, OSAMU、SITAGAKU, TEHTSUO、FURUT+

  DOI：——

  日期：——