5-azido-5-deoxy-1,2-O-isopropylidene-6-O-methyl-3-O-(methoxymethyl)-α-D-glucofuranose | 192806-40-9

• 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-1,2-O-isopropylidene-6-O-methyl-3-O-(methoxymethyl)-α-D-glucofuranose
• CAS: 192806-40-9
• 化学式: C₁₂H₂₁N₃O₆
• 分子量: 303.315
• InChiKey: XMWRXKBUEQKWTG-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.18
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104.14
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-6-O-methyl-3-O-(methoxymethyl)-α-D-glucofuranose 在 Amberlite IR-120 [H⁺] ion-exchange resin 作用下， 以 水 、 乙腈 为溶剂， 以77%的产率得到5-azido-5-deoxy-6-O-methyl-D-glucofuranose
  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 四丁基氟化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-methyl-3-O-(methoxymethyl)-α-D-glucofuranose
  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