1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine | 860640-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine
• 英文别名: (1S,2R,3R,4S,6R)-4,6-diazido-3-[[(2R,3R,6S)-3-azido-6-(azidomethyl)-3,6-dihydro-2H-pyran-2-yl]oxy]cyclohexane-1,2-diol
• CAS: 860640-70-6
• 化学式: C₁₂H₁₆N₁₂O₄
• 分子量: 392.337
• InChiKey: NGRMXVQSINQTEH-MIRCGDSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine 在 sodium hydroxide 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 N,N-二异丙基乙胺 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 (2S,3R,4S,5S,6R)-5-amino-2-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[[(2R,3R,6S)-3-amino-6-(aminomethyl)-3,6-dihydro-2H-pyran-2-yl]oxy]-6-hydroxycyclohexyl]oxy-6-methyloxane-3,4-diol
  参考文献：
  名称：

  Novel Method for the Synthesis of 3′,4′‐Dideoxygenated Pyranmycin and Kanamycin Compounds, and Studies of Their Antibacterial Activity Against Aminoglycoside‐Resistant Bacteria

  摘要：

  A novel protocol for converting a trans-diol to an alkene under mild conditions was developed. This method let to the synthesis of a 3',4'-dideoxykanamycin (dibekacin) analog and a 3',4'-dideoxypyranmycin that were found to be active against aminoglycoside-resistant bacteria.

  DOI：

  10.1081/car-200059968
• 作为产物：
  描述：

  [(2R,3R,4R,5R,6R)-6-[(3aS,4R,5S,7R,7aS)-5,7-diazidospiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-5-azido-2-(azidomethyl)-4-(trifluoromethylsulfonyloxy)oxan-3-yl] trifluoromethanesulfonate 在 sodium thiosulfate 、 溶剂黄146 、 sodium iodide 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 1,3,2',6'-tetraazido-3',4'-dideoxy-3'-enoneamine
  参考文献：
  名称：

  Novel Method for the Synthesis of 3′,4′‐Dideoxygenated Pyranmycin and Kanamycin Compounds, and Studies of Their Antibacterial Activity Against Aminoglycoside‐Resistant Bacteria

  摘要：

  A novel protocol for converting a trans-diol to an alkene under mild conditions was developed. This method let to the synthesis of a 3',4'-dideoxykanamycin (dibekacin) analog and a 3',4'-dideoxypyranmycin that were found to be active against aminoglycoside-resistant bacteria.

  DOI：

  10.1081/car-200059968

文献信息

• Synthesis of novel aminoglycosides via allylic azide rearrangement for investigating the significance of 2′-amino group
  作者：Jianjun Zhang、Anthony Litke、Katherine Keller、Ravi Rai、Cheng-Wei Tom Chang

  DOI：10.1016/j.bmc.2010.01.027

  日期：2010.2

  Using allylic azide rearrangement, a convenient method has been developed for the synthesis of 2′,3′-dideoxyaminoglycosides that are, otherwise, difficult to be prepared. The antibacterial activity of these novel aminoglycosides also confirms the indispensable role of 2′-NH2 group for both neomycin and kanamycin classes of aminoglycosides. A novel structural motif containing the hexylaminocarbonyl

  使用烯丙基叠氮化物重排，已经开发了方便的方法来合成否则难以制备的2'，3'-二脱氧氨基糖苷。这些新型氨基糖苷类的抗菌活性也证实了2'-NH 2基团对于新霉素类和卡那霉素类氨基糖苷类都起着不可或缺的作用。在2'，3'-二脱氧亚胺的O -5和/或O -6处含有己氨基羰基的新型结构基序可以导致产生新的抗药性氨基糖苷。
• Design and Synthesis of Pyrankacin:  A Pyranmycin Class of Broad-Spectrum Aminoglycoside Antibiotic
  作者：Ravi Rai、Hsiao-Nung Chen、Przemyslaw G. Czyryca、Jie Li、Cheng-Wei Tom Chang

  DOI：10.1021/ol0529750

  日期：2006.3.2

  A novel broad-spectrum aminoglycoside antibiotic, pyrankacin, has been prepared. In addition to the synthetic innovation in dideoxygenation and regioselective Staudinger reduction, we have obtained prominent antibacterial activity against several clinically important pathogens in the course of this work.

  已经制备了一种新型的广谱氨基糖苷类抗生素吡喃卡星。除了在双脱氧和区域选择性施陶丁格还原方面的合成创新外，我们在这项工作过程中还获得了对几种临床上重要病原体的显着抗菌活性。
• Novel anti bacterial compounds
  申请人：Chang Tom Cheng-Wei

  公开号：US20060234961A1

  公开（公告）日：2006-10-19

  The invention relates to novel paranmycin compounds that have activity against gram positive and gram negative bacteria, preferably bacteria that are resistant to other antibiotics. Paranmycins are of the general formula

  本发明涉及新型的帕拉霉素化合物，其具有对革兰氏阳性和革兰氏阴性细菌的活性，更好地对抗其他抗生素耐药的细菌。帕拉霉素的一般化学式为：