3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B | 78740-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B
• CAS: 78740-48-4
• 化学式: C₄₃H₇₇N₅O₁₈
• 分子量: 952.107
• InChiKey: WQPNLLHSKKFQMT-VUFJYASUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  66.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  309.49
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B 在 吡啶 、 重铬酸吡啶 、 3 A molecular sieve 、 水 、 sodium methylate 、 对甲苯磺酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -20.0~50.0 ℃ 、4.0 kPa 条件下， 反应 32.5h， 生成
  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：

  地贝卡星 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.67h， 以96%的产率得到3',4'-dideoxy-1,3,2',6',3''-pentakis(N-tert-butoxycarbonyl)kanamycin B
  参考文献：
  名称：

  Synthesis of 5-deoxy-5-epifluoro derivatives of arbekacin, amikacin, and 1-N-[(S)-4-amino-2-hydroxybutanoyl]tobramycin (study on structure — toxicity relationships)

  摘要：

  As part of a study on fluorination-toxicity relationships for aminoglycoside antibiotics, 5,3'-dideoxy-5-epifluorokanamycin B (10), 5,3',4'-trideoxy-5-epifluorokanamycin B (11), 1-N-[(S)-4-amino-2-hydroxybutanoyl]-5-deoxy-5-epifluorotobramycin (19), 5-deoxy-5-epifluoroarbekacin (20), and 5-deoxy-5-epifluoroamikacin (21) have been prepared. The acute toxicities of these three 5-deoxy-5-epifluoro compounds showed values almost identical or similar to those for arbekacin (ABK) and amikacin (15), making a sharp contrast with the toxicities of the corresponding 5-deoxy-5-fluoro derivatives. This fact is explained on the basis of basicity changes (retention for the 5-epifluoro derivatives and reduction for the 5-fluoro derivatives) at the H2N-3 groups of the fluorinated compounds compared to the parent compounds; this hypothesis was substantiated by the pKa values at the H3N+-1, 3 groups (determined by the shift changes depending on pD values at C-2 and C-4, 6 in their C-13 NMR spectral of 2,5-dideoxy-5-epifluorostreptamine (23) and 2,5-dideoxy-5-fluorostreptamine (24), chosen as model compounds, and 2-deoxystreptamine (DST).

  DOI：

  10.1016/0008-6215(95)00123-b