(N-acetyl-β-D-glucopyranosylamine)uronamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (N-acetyl-β-D-glucopyranosylamine)uronamide
• 英文别名: (2S,3S,4S,5R,6R)-6-acetamido-3,4,5-trihydroxyoxane-2-carboxamide
• 化学式: C₈H₁₄N₂O₆
• 分子量: 234.209
• InChiKey: JNGQZEVUIXNCMK-UQGZVRACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,2R,3R,5S)-2,3,6-三羟基-4,8-二氧杂双环[3.3.0]辛烷-7-酮 、 乙酸酐 在 氨 、 碳酸氢铵 作用下， 以65%的产率得到ammonium (β-D-glucopyranosylamine)uronate
  参考文献：
  名称：

  Synthesis ofN-chioroacetyl-?-glycopyranosylamines, derivatives of monosaccharides and lactose

  摘要：

  N-Chloroacetyl-beta-glycosylamines were synthesized from various monosaccharides (hexoses, pentoses, deoxysugars, uronic acids, and sugar phosphates) and a disaccharide (lactose) by N-acylation of the corresponding beta-glycosylamines with chloroacetic anhydride in DMF. In some cases, treatment of monosaccharides with NH3 in the presence of (NH4)CO3 in MeOH or aqueous MeOH was more efficient than the methods previously described, as it gave beta-glycosylamines in higher yields.

  DOI：

  10.1007/bf01431821