1-deoxy-1-(2-formyl-1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose | 1338805-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1-deoxy-1-(2-formyl-1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• 英文别名: 1-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl]pyrrole-2-carbaldehyde
• CAS: 1338805-40-5
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: NTANFBZLZKXIMN-WVZRYYJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  果糖二丙酮 在 磺酰氯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 11.0h， 生成 1-deoxy-1-(2-formyl-1H-pyrrol-1-yl)-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis of Novel N-carbohydrate-derived Heterocyclic Compounds by Nucleophilic Substitution Reaction of Carbohydrate Imidazole-1-sulfonates

  摘要：

  The nucleophilic substitution reaction of carbohydrate imidazole-1-sulfonates with pyrrole and other nitrogen heterocyclic compounds is reported for the first time. Several novel N-carbohydrate-derived heterocyclic compounds have been prepared by this displacement reaction. The desired carbon-nitrogen bond formation proceeds under mild conditions to generate the coupling products in good yields with readily available and inexpensive reagents. This method is particularly suitable for carbohydrate imidazole-1-sulfonates of primary alcohols. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the free supplemental file.

  DOI：

  10.1080/07328303.2011.605193