(1R,2S,3R,4R)-1-nonyl-2,3-isopropylidenedioxy-4-hydroxymethyl pyrrolidine acetate salt

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4R)-1-nonyl-2,3-isopropylidenedioxy-4-hydroxymethyl pyrrolidine acetate salt
• 英文别名: 1-α-nonyl-2,3-O-isopropylidene-1,4-imino-1,4-dideoxy-D-ribitol acetate salt；(2R,3S,4R,5R)-2-nonyl-3,4-isopropylidenedioxy-5-hydroxymethylpyrrolidine acetate salt；[(3aR,4R,6R,6aS)-2,2-dimethyl-6-nonyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl]methanol;acetic acid
• 化学式: C₂H₄O₂*C₁₇H₃₃NO₃
• 分子量: 359.506
• InChiKey: COAUYWVJSFNZCT-XPRGAJIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4R)-1-nonyl-2,3-isopropylidenedioxy-4-hydroxymethyl pyrrolidine acetate salt 在 palladium on activated charcoal 甲醇 、 氢气 、 溶剂黄146 作用下， 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-nonyl-5-O-methanesulfonyl-2,3-O-isopropylidene-L-lyxose 在 Amberlyst A₂₁-IR 、 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 (1R,2S,3R,4R)-1-nonyl-2,3-isopropylidenedioxy-4-hydroxymethyl pyrrolidine acetate 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

文献信息

• Combinatorial library approach to iminocyclitols with biological activity
  申请人：Moriarity M. Robert

  公开号：US20070088164A1

  公开（公告）日：2007-04-19

  A method of synthesizing stereochemically defined iminocyclitol comprises replacing an intraring oxygen in a cyclic sugar by an intraring imine to form an iminocyclitol, wherein said iminocyclitol has a defined stereochemical configuration different from a stereochemical configuration of the cyclic sugar. The invention also provides combinatorial libraries of iminocyclitol compounds, allowing for diverse C1 and N-substitution. In addition, provided are methods of treating viral infections with iminocyclitols compounds.

  合成立体化定义的亚胺环糖醇的方法包括通过在环糖中替换环内氧原子为环内亚胺来形成亚胺环糖醇，其中所述亚胺环糖醇具有与环糖不同的定义的立体化配置。该发明还提供了亚胺环糖醇化合物的组合库，允许多样的C1和N取代。此外，还提供了使用亚胺环糖醇化合物治疗病毒感染的方法。
• <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.