4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-5,3'-dideoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B | 119783-95-8

• 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: 4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-5,3'-dideoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B
• 英文别名: [(2R,3S,5R,6R)-6-[(1R,2S,3S,4R,6S)-3-[(4aR,6R,7R,8S,8aS)-7-acetyloxy-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]-2-[[(4-methylphenyl)sulfonylamino]methyl]oxan-3-yl] acetate
• CAS: 119783-95-8
• 化学式: C₆₃H₇₈FN₅O₂₀S₅
• 分子量: 1404.66
• InChiKey: PKGJEORNVMWSIP-QZTPXJLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  94.0
• 可旋转键数：
  22.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.49
• 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：

  4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-5,3'-dideoxy-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-2-[(1S,2S,3R,4S,6R)-3-((2R,3R,5S,6R)-5-acetoxy-3-amino-6-aminomethyl-tetrahydro-pyran-2-yloxy)-4,6-diamino-2-fluoro-cyclohexyloxy]-6-acetoxymethyl-4-amino-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：

  4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-3'-deoxy-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 苯 为溶剂， 反应 2.0h， 生成 4',2''-di-O-acetyl-4'',6''-O-cyclohexylidene-5,3'-dideoxy-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：——