(1S,2R,3S,4S)-1-nonyl-N-nonyl-2,3-diol-4-hydroxymethyl pyrrolidine trifluoroacetate salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2R,3S,4S)-1-nonyl-N-nonyl-2,3-diol-4-hydroxymethyl pyrrolidine trifluoroacetate salt
• 英文别名: 1-β-nonyl-N-nonyl-1,4-imino-1,4-dideoxy-L-ribitol trifluoroacetate salt；(2S,3S,4R,5S)-2-(hydroxymethyl)-1,5-di(nonyl)pyrrolidine-3,4-diol;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₂₃H₄₇NO₃
• 分子量: 499.655
• InChiKey: AAPQKEQLYPZONA-IEFSPCKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S)-1-nonyl-N-nonyl-2,3-diol-4-hydroxymethyl pyrrolidine trifluoroacetate salt 在 Amberlyst A₂₁-IR 作用下， 以 甲醇 为溶剂， 以96%的产率得到(1S,2R,3S,4S)-1-nonyl-N-nonyl-2,3-diol-4-hydroxymethyl pyrrolidine
  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：

  (3R,4S,5S)-2-nonyl-3,4-isopropylidenedioxy-5-hydroxymethyl-1-pyrroline 在 palladium on activated charcoal 甲醇 、 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 (1S,2R,3S,4S)-1-nonyl-N-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

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.