[(3aR,4R,6R,6aS)-2,2-dimethyl-5,6-di(nonyl)-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methanol | 934346-93-7

• 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-5,6-di(nonyl)-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methanol
• CAS: 934346-93-7
• 化学式: C₂₆H₅₁NO₃
• 分子量: 425.696
• InChiKey: DWIVUFREOOFWNN-ZKGSSEMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,6aS)-2,2-dimethyl-5,6-di(nonyl)-3a,4,6,6a-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：

  (2S,3R,4R)-1-nonyl-2,3-isopropylidenedioxy-4-hydroxymethyl-1-pyrroline 在 palladium on activated charcoal 甲醇 、 Amberlyst A₂₁-IR 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 [(3aR,4R,6R,6aS)-2,2-dimethyl-5,6-di(nonyl)-3a,4,6,6a-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

文献信息

• <i>exo</i>-Imino to <i>endo</i>-Iminocyclitol Rearrangement. A General Route to Five-Membered Antiviral Azasugars
  作者：Robert M. Moriarty、Carmen I. Mitan、Norica Branzǎ-Nichita、Kenneth R. Phares、Damon Parrish

  DOI：10.1021/ol061071r

  日期：2006.8.1

  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.