penta-N-tosyldibekacin | 64879-65-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: penta-N-tosyldibekacin
• 英文别名: 3',4'-dideoxy-5-fluoro-1,3,2',6',3''-penta-N-tosylkanamycin B
• CAS: 64879-65-8
• 化学式: C₅₃H₆₇N₅O₁₈S₅
• 分子量: 1222.47
• InChiKey: RWMHBIOAWXJGKC-CGDGIBQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  81.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  348.69
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  penta-N-tosyldibekacin 在 对甲苯磺酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2''-O-acetyl-4'',6''-O-benzylidene-1,3,2',6',3''-penta-N-tosyldibekacin
  参考文献：
  名称：

  Synthesis of 2″-acylamido derivatives of 2″-amino-5,2″-dideoxy-5-epi-5-fluorodibekacin and a study on the structures of 5-fluorinated dibekacin analogs by 13C NMR

  摘要：

  Several 2 ''-amino-2 ''-deoxy and 2 ''-acylamido-2 ''-deoxy derivatives (15-21) of 5-deoxy-5-epi-5-fluorodibekacin have been prepared, introducing the 2 ''-NH2, up via oxidation-methoxyimination-reduction processes. The C-4 and C-6 chemical shifts in the C-13 NMR spectra of several 5-fluorinated kanamycin analogs have been studied, and the difference in shifts was explained on the basis of F-5-O-4 and F-5-O-6 distances estimated by MOPAC93/PM3 calculations on related model compounds. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00031-1

文献信息

• Synthesis of 5-deoxy-5-fluoro and 5-deoxy-5,5-difluoro derivatives of kanamycin B in its analogs. Study on structure-toxicity relationships
  作者：Tetsuo Shitara、Yoshihiko Kobayashi、Tsutomu Tsuchiya、Sumio Umezawa

  DOI：10.1016/0008-6215(92)80060-e

  日期：1992.8

  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.