5-azido-5-deoxy-6-O-methyl-D-fructose | 192806-46-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-6-O-methyl-D-fructose
• CAS: 192806-46-5
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: BZZMQXJBHUQYNC-QPPQHZFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  135.75
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-6-O-methyl-D-fructose 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以65%的产率得到2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol
  参考文献：
  名称：

  Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol: Syntheses and glucosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-d-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-d-mannitol

  摘要：

  1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannit and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconversion reactions as the key steps of the syntheses. Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00099-2
• 作为产物：
  描述：

  5-azido-5-deoxy-6-O-dimethyl(1,1,2-trimethylpropyl)silyl-1,2-O-isopropylidene-α-D-glucofuranose 在 Amberlite IR-120 [H⁺] ion-exchange resin 、 Sweetzyme T (immobilised glucose isomerase (EC 5.3.1.5)) 、 四丁基氟化铵 、 sodium hydride 、 magnesium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 5-azido-5-deoxy-6-O-methyl-D-fructose
  参考文献：
  名称：

  Two isosteric fluorinated derivatives of the powerful glucosidase inhibitors, 1-deoxynojirimycin and 2,5-dideoxy-2,5-imino-d-mannitol: Syntheses and glucosidase-inhibitory activities of 1,2,5-trideoxy-2-fluoro-1,5-imino-d-glucitol and of 1,2,5-trideoxy-1-fluoro-2,5-imino-d-mannitol

  摘要：

  1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol, the 2-deoxyfluoro derivative of 1-deoxynojirimycin, as well as 1,2,5-trideoxy-1-fluoro-2,5-imino-D-mannit and 2,5-dideoxy-2,5-imino-1-O-methyl-D-mannitol, two new analogues of the natural product and powerful glucosidase inhibitor 2,5-dideoxy-2,5-imino-D-mannitol, were synthesised featuring glucose isomerase-catalysed aldose-ketose interconversion reactions as the key steps of the syntheses. Results of inhibition studies conducted with these compounds and previously obtained deoxyfluoro derivatives of 1-deoxynojirimycin, employing glucosidases from various sources, showed that the replacement of a hydroxyl function by fluorine caused an impairment of the inhibitory potency. This effect was smallest for the hydroxyl group at C-6 and up to four orders of magnitude larger for replacements at C-2 and C-3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00099-2