((3aS,4S,6aR)-6-Decyl-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol | 909703-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aS,4S,6aR)-6-Decyl-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol
• CAS: 909703-17-9
• 化学式: C₁₈H₃₃NO₃
• 分子量: 311.465
• InChiKey: BILHCGZJDXZBHG-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  51.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((3aS,4S,6aR)-6-Decyl-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-methanol 在 palladium on activated charcoal 氢气 作用下， 以 水 为溶剂， 生成 (1S,2R,3S,4S)-1-nonyl-2,3-diol-4-hydroxymethyl pyrrolidine trifluoroacetate salt
  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：

  2,3-O-isopropylidene-5-O-methanesulfonyl-D-lyxono-1,4-lactone 、 alkaline earth salt of/the/ methylsulfuric acid 在 氨 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 ((3aS,4S,6aR)-6-Decyl-2,2-dimethyl-4,6a-dihydro-3aH-[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