2,3:4,5-di-O-isopropylidene-1-O-(1H-imidazol-1-ylsulfonyl)-β-D-fructopyranose | 1338805-38-1

• 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: 2,3:4,5-di-O-isopropylidene-1-O-(1H-imidazol-1-ylsulfonyl)-β-D-fructopyranose
• 英文别名: [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl imidazole-1-sulfonate
• CAS: 1338805-38-1
• 化学式: C₁₅H₂₂N₂O₈S
• 分子量: 390.414
• InChiKey: HGIIBTUZEWJTBN-FJJYHAOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  苯并咪唑 、 2,3:4,5-di-O-isopropylidene-1-O-(1H-imidazol-1-ylsulfonyl)-β-D-fructopyranose 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 9.0h， 以80%的产率得到1-deoxy-1-(1H-benzimidazol-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
• 作为产物：
  描述：

  咪唑 、 果糖二丙酮 在 磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到2,3:4,5-di-O-isopropylidene-1-O-(1H-imidazol-1-ylsulfonyl)-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