5-O-(2,4-di-O-acetyl-3-O-allyl-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine | 675616-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(2,4-di-O-acetyl-3-O-allyl-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine
• 英文别名: [(2R,3R,4S,5R,6S)-5-acetyloxy-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-[(2R,3R,4R,5R,6R)-3-azido-6-(azidomethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-6-phenylmethoxycyclohexyl]oxy-2-methyl-4-prop-2-enoxyoxan-3-yl] acetate
• CAS: 675616-55-4
• 化学式: C₄₆H₅₄N₁₂O₁₂
• 分子量: 967.008
• InChiKey: LPSOVEFYHHPICH-LMARURRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  184
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  5-O-(2,4-di-O-acetyl-3-O-allyl-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine 在 palladium dihydroxide 氨 、 氢气 、 potassium carbonate 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 14.0h， 生成 5-O-(3-O-(3-fluoropropyl)-6-deoxy-β-D-glucopyranosyl)neamine tetra(acetic acid) salt
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r
• 作为产物：
  描述：

  3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 三氟化硼乙醚 、 乙酸肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-O-(2,4-di-O-acetyl-3-O-allyl-6-deoxy-β-D-glucopyranosyl)-6,3',4'-tri-O-benzyl-1,3,2',6'-tetraazidoneamine
  参考文献：
  名称：

  Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin

  摘要：

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

  DOI：

  10.1021/jo035290r