N-((1S,2R,3S,4R)-1-Hydrazonomethyl-2,3,4,5-tetrahydroxy-pentyl)-acetamide | 202986-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((1S,2R,3S,4R)-1-Hydrazonomethyl-2,3,4,5-tetrahydroxy-pentyl)-acetamide
• CAS: 202986-41-2
• 化学式: C₈H₁₇N₃O₅
• 分子量: 235.24
• InChiKey: NXANDIBYEQQFBT-CWVSWYGYSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.49
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  148.4
• 氢给体数：
  6.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  对甲苯异硫氰酸酯 、 N-((1S,2R,3S,4R)-1-Hydrazonomethyl-2,3,4,5-tetrahydroxy-pentyl)-acetamide 以 甲醇 、 水 为溶剂， 反应 3.0h， 以70%的产率得到2-acetamido-2-deoxy-D-glucose 4-tolylthiosemicarbazone
  参考文献：
  名称：

  NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies

  摘要：

  To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.

  DOI：

  10.1080/07328309808005766
• 作为产物：
  描述：

  D-GlcNAc 在 一水合肼 作用下， 以 水 为溶剂， 反应 6.0h， 生成 乙酰肼 、 2-amino-2-deoxy-D-glucose hydrazone 、 N-((1S,2R,3S,4R)-1-Hydrazonomethyl-2,3,4,5-tetrahydroxy-pentyl)-acetamide
  参考文献：
  名称：

  NMR Studies of Saccharide Hydrazones, Thiosemicarbazones and Azines: Model Compounds for Immobilisation Studies

  摘要：

  To evaluate possible chemical strategies for the solid-phase immobilization of sugars, studies on the formation and stability of hydrazones, thiosemicarbazones and azines of D-glucose and 2-acetamido-2-deoxy-D-glucose, and the subsequent release of sugars, were carried out. Hydrazone formation was observed to occur under milder conditions than previously reported, thereby minimising the accompanying N-deacetylation which occurs with N-acetamido sugars. The cyclic beta-pyranosyl structures of the saccharide hydrazones, thiosemicarbazones and azines were the preferred isomers in aqueous solution.

  DOI：

  10.1080/07328309808005766