phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside | 868258-64-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-4-azido-2-methyl-5-phenylmethoxy-6-phenylsulfanyloxan-3-yl] benzoate
• CAS: 868258-64-4
• 化学式: C₂₆H₂₅N₃O₄S
• 分子量: 475.568
• InChiKey: XARWDIJCGNMZCR-CTCBWZERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside 在 sodium hydroxide 、 N-碘代丁二酰亚胺 、 sodium methylate 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (2R,3S,4R,5R,6R)-5-Amino-2-aminomethyl-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-((2R,3R,4S,5S,6R)-4-amino-3-benzyloxy-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-hydroxy-cyclohexyloxy]-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides

  摘要：

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.

  DOI：

  10.1021/jm050368c
• 作为产物：
  描述：

  phenyl 3,4-di-O-acetyl-2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside 在 4-二甲氨基吡啶 、 sodium azide 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 phenyl 3-azido-4-O-benzoyl-2-O-benzyl-3,6-dideoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides

  摘要：

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.

  DOI：

  10.1021/jm050368c

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。
• Chemical synthesis of the pentasaccharide repeating unit of the O-antigen from Escherichia coli strain SDLZB008 in the form of its 2-aminoethyl glycoside
  作者：Sakshi Balasaria、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2022.108734

  日期：2023.1

  monosaccharide derivatives ensuring desired stereochemical outcome up on glycosylations. 2-Aminoethyl glycoside is incorporated at the reducing end of the target pentasaccharide. The terminal free amine may be used for further conjugation with suitable aglycon without hampering the reducing end stereochemistry. The rare D-Fucp3NAc moiety is incorporated through the corresponding 3-azido derivative derived

  来自大肠杆菌菌株 SDLZB008 的O抗原的五糖重复单元的化学合成是通过使用合理保护的单糖衍生物的线性策略完成的，确保糖基化所需的立体化学结果。2-氨基乙基糖苷结合在目标五糖的还原端。末端游离胺可用于与合适的糖苷配基进一步缀合而不妨碍还原端立体化学。罕见的 D-Fuc p 3NAc 部分通过衍生自已知 3-叠氮基奎诺糖衍生物的相应 3-叠氮基衍生物并入。
• Glycodiversification for the Optimization of the Kanamycin Class Aminoglycosides
  作者：Jinhua Wang、Jie Li、Hsiao-Nung Chen、Huiwen Chang、Christabel Tomla Tanifum、Hsiu-Hsiang Liu、Przemyslaw G. Czyryca、Cheng-Wei Tom Chang

  DOI：10.1021/jm050368c

  日期：2005.10.1

  In an effort to optimize the antibacterial activity of kanamycin class aminoglycoside antibiotics, we have accomplished the synthesis and antibacterial assay of new kanamycin B analogues. A rationale-based glycodiversification strategy was employed. The activity of the lead is comparable to that of commercially available kanamycin. These new members, however, were found to be inactive against aminoglycoside resistant bacteria. Molecular modeling was used to provide the explanation. Thus, a new strategy for structural modifications of kanamycin class aminoglycosides is suggested.