((3aR,4R,6R,6aS)-2,2-Dimethyl-5-nonyl-6-octyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol | 934346-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,4R,6R,6aS)-2,2-Dimethyl-5-nonyl-6-octyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol
• CAS: 934346-91-5
• 化学式: C₂₅H₄₉NO₃
• 分子量: 411.669
• InChiKey: LJGBHWQWLLRJID-JLLPCOHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  29.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((3aR,4R,6R,6aS)-2,2-Dimethyl-5-nonyl-6-octyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol 、 三氟乙酸酐 以 水 为溶剂， 生成
  参考文献：
  名称：

  exo-Imino to endo-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars

  摘要：

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.

  DOI：

  10.1021/ol061071r
• 作为产物：
  描述：

  1-octyl-5-O-methanesulfonyl-2,3-O-isopropylidene-L-lyxose 在 palladium on activated charcoal 甲醇 、 Amberlyst A₂₁-IR 、 氨 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 ((3aR,4R,6R,6aS)-2,2-Dimethyl-5-nonyl-6-octyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol
  参考文献：
  名称：

  exo-Imino to endo-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars

  摘要：

  A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C-1- and N-substitution, and the potential for a three-component combinatorial process. The key step is inversion at the C-4 stereocenter (L-lyxo sugar -> D-ribono azasugar). The exo-imino to endo-iminocyclitol process was extended to the D-lyxo and the D- and L-hexose series. Some analogues were found to be more potent than N-butyl DNJ and N-nonyl DNJ in antiviral activity.

  DOI：

  10.1021/ol061071r