2'',4'',6''-tri-O-acetyl-1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3',4'-trideoxy-5,5-difluorokanamycin B | 142860-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'',4'',6''-tri-O-acetyl-1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3',4'-trideoxy-5,5-difluorokanamycin B
• CAS: 142860-01-3
• 化学式: C₆₄H₇₁F₂N₅O₂₀
• 分子量: 1268.29
• InChiKey: WKIYWCIKBLHNLJ-ZJGSICKNSA-N

反应信息

• 作为产物：
  描述：

  2'',4'',6''-tri-O-acetyl-1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3',4'-trideoxy-5-oxokanamycin B 在 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， 以65%的产率得到2'',4'',6''-tri-O-acetyl-1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-5,3',4'-trideoxy-5,5-difluorokanamycin 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