4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin | 189157-35-5

• 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: 4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
• CAS: 189157-35-5
• 化学式: C₅₃H₉₁FN₆O₁₉
• 分子量: 1135.33
• InChiKey: GSHJLIWILXFLCQ-QTLPOITASA-N

反应信息

• 作为反应物：
  描述：

  4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 戴斯-马丁氧化剂 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4'',6''-O-cyclohexylidene-5,2'''-dideoxy-5-epi-5-fluoro-2'''-oxo-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
  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：

  2'',2'''-di-O-benzoyl-4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以89%的产率得到4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
  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