(2R,3R,4S,5S,6R)-2-Allylamino-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-2-Allylamino-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: 1-(Allylamino)-1-deoxy-beta-d-glucopyranose；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(prop-2-enylamino)oxane-3,4,5-triol
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: HYHFUUJWYZCDBC-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  102
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6R)-2-Allylamino-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 以 吡啶 为溶剂， 生成 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[acetyl(prop-2-enyl)amino]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  An Efficient Synthesis of N-Allylglycosylamides from Unprotected Carbohydrates

  摘要：

  Synthetic, multivalent, carbohydrate assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N-allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N-allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis(x) and sulfo Lewis(x) have been derivatized by this process.

  DOI：

  10.1021/jo9522522
• 作为产物：
  描述：

  D-葡萄糖 、 丙烯胺 反应 72.0h， 生成 (2R,3R,4S,5S,6R)-2-Allylamino-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  An Efficient Synthesis of N-Allylglycosylamides from Unprotected Carbohydrates

  摘要：

  Synthetic, multivalent, carbohydrate assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N-allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N-allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis(x) and sulfo Lewis(x) have been derivatized by this process.

  DOI：

  10.1021/jo9522522