2'''-O-acetyl-4'',6''-O-cyclohexylidene-5,2''-dideoxy-5-epi-5-fluoro-2''-oxo-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin | 189157-38-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 2'''-O-acetyl-4'',6''-O-cyclohexylidene-5,2''-dideoxy-5-epi-5-fluoro-2''-oxo-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
• CAS: 189157-38-8
• 化学式: C₅₅H₉₁FN₆O₂₀
• 分子量: 1175.35
• InChiKey: RNKDSCNRAYOBFM-KABIEPOCSA-N

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 2'''-O-acetyl-4'',6''-O-cyclohexylidene-5,2''-dideoxy-5-epi-5-fluoro-2''-oxo-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 水 、 sodium methylate 作用下， 生成 (S)-4-Amino-N-[(1R,2S,3R,4R,5S)-5-amino-4-((2R,3R,6S)-3-amino-6-aminomethyl-tetrahydro-pyran-2-yloxy)-2-((2R,4S,5S,6R)-4-amino-3,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-fluoro-cyclohexyl]-2-hydroxy-butyramide; compound with trifluoro-acetic acid
  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'''-O-acetyl-4'',6''-O-cyclohexylidene-5-deoxy-5-epi-5-fluoro-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 乙酸酐 、 二甲基亚砜 作用下， 反应 48.0h， 以85%的产率得到2'''-O-acetyl-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