6-azido-3,6-dideoxy-1,2-O-isopropylidene-β-D-arabino-hexofuranose | 284031-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-3,6-dideoxy-1,2-O-isopropylidene-β-D-arabino-hexofuranose
• CAS: 284031-20-5
• 化学式: C₉H₁₅N₃O₄
• 分子量: 229.236
• InChiKey: LVYLBTPCNMTJDG-KVPKETBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-azido-3,6-dideoxy-1,2-O-isopropylidene-β-D-arabino-hexofuranose 在 palladium on activated charcoal Amberlite IR-120 (H⁽¹⁺⁾) 、 氢气 作用下， 以 水 、 乙腈 、 甲醇 为溶剂， 20.0~40.0 ℃ 、3.0 MPa 条件下， 反应 16.0h， 生成 1,3,6-trideoxy-1,6-imino-D-arabino-hexitol
  参考文献：
  名称：

  Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

  摘要：

  Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00018-5
• 作为产物：
  描述：

  3-deoxy-D-arabino-hexono-1,4-lactone 在 camphor-10-sulfonic acid sodium azide 、 2-甲基-2-丁烯 、 dimethyl sulfide borane 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 6-azido-3,6-dideoxy-1,2-O-isopropylidene-β-D-arabino-hexofuranose
  参考文献：
  名称：

  Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

  摘要：

  Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-l,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-riho-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00018-5