2'',3''-O,N-carbonyl-4'',6''-O-cyclohexylidene-5-deoxy-5,2''-diepi-5-fluoro-1,3,2',6'-tetrakis(N-tert-butoxycarbonyl)dibekacin | 189157-27-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2'',3''-O,N-carbonyl-4'',6''-O-cyclohexylidene-5-deoxy-5,2''-diepi-5-fluoro-1,3,2',6'-tetrakis(N-tert-butoxycarbonyl)dibekacin
• CAS: 189157-27-5
• 化学式: C₄₅H₇₄FN₅O₁₆
• 分子量: 960.105
• InChiKey: GPKIUEOVXTUNNM-KDSANECTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  67.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  247.03
• 氢给体数：
  5.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  2'',3''-O,N-carbonyl-4'',6''-O-cyclohexylidene-5-deoxy-5,2''-diepi-5-fluoro-1,3,2',6'-tetrakis(N-tert-butoxycarbonyl)dibekacin 在 sodium hydroxide 、 三氟乙酸 作用下， 生成 (2R,3S,4S,5S,6R)-4-amino-2-[(1S,2R,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-fluorocyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
  参考文献：
  名称：

  Synthesis of 2″-oxidized derivatives of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin, and study on structure-chemical shift relationships of urethane(or amide)-type NH protons in synthetic intermediates

  摘要：

  Three 2''-modified dibekacin-analogs have been prepared as potential compounds active against resistant bacteria producing 2''-O-phosphotransferases; one is 5-deoxy-5,2''-diepi-5-fluorodibekacin (9) prepared from a suitably protected 2''-O-triflyl derivative through the 2'',3''-cyclic carbamate, and the others are 2''-oxo derivatives (12 and 22, both as the hydrate) of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin prepared through oxidation at C-2'' of suitably protected derivatives. Relationships between the t-butoxycarbonyl(= Boc)-NH-shifts of per-N-Boc synthetic intermediates and their structures were studied. It was found that the shifts, measured in pyridine-d(5) at 80 degrees C, which spread over a close range (delta 6-7 ppm), are sensitively influenced by nearby and surrounding groups around the BocNH group in respect of electron-withdrawing character, hydrogen bonding (BocNH ... acceptor), and also solvent effects (BocNH ... NC5H5). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00318-7
• 作为产物：
  描述：

  环己酮二甲缩酮 在 吡啶 、 sodium methylate 、 sodium acetate 、 对甲苯磺酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -20.0~80.0 ℃ 、4.0 kPa 条件下， 反应 29.0h， 生成 2'',3''-O,N-carbonyl-4'',6''-O-cyclohexylidene-5-deoxy-5,2''-diepi-5-fluoro-1,3,2',6'-tetrakis(N-tert-butoxycarbonyl)dibekacin
  参考文献：
  名称：

  Synthesis of 2″-oxidized derivatives of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin, and study on structure-chemical shift relationships of urethane(or amide)-type NH protons in synthetic intermediates

  摘要：

  Three 2''-modified dibekacin-analogs have been prepared as potential compounds active against resistant bacteria producing 2''-O-phosphotransferases; one is 5-deoxy-5,2''-diepi-5-fluorodibekacin (9) prepared from a suitably protected 2''-O-triflyl derivative through the 2'',3''-cyclic carbamate, and the others are 2''-oxo derivatives (12 and 22, both as the hydrate) of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin prepared through oxidation at C-2'' of suitably protected derivatives. Relationships between the t-butoxycarbonyl(= Boc)-NH-shifts of per-N-Boc synthetic intermediates and their structures were studied. It was found that the shifts, measured in pyridine-d(5) at 80 degrees C, which spread over a close range (delta 6-7 ppm), are sensitively influenced by nearby and surrounding groups around the BocNH group in respect of electron-withdrawing character, hydrogen bonding (BocNH ... acceptor), and also solvent effects (BocNH ... NC5H5). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00318-7