1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole | 1454311-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole
• CAS: 1454311-01-3
• 化学式: C₂₀H₂₄N₄O₉
• 分子量: 464.432
• InChiKey: QTIHHVSRMDBKCQ-WAPOTWQKSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157.17
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-苯丙醇 、 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole 在 cobalt(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到3-苯基丙基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Glycosylated derivatives of substituted hydroxylamine. II. The phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine

  摘要：

  The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis acids resulted in alkyl-O-glucosaminides with the 1,2-trans-configuration of the glycoside bond. Other glucosaminides of substituted hydroxylamine were shown not to react under these conditions. The structures of the synthesized glucosaminides were confirmed by H-1 NMR spectroscopy and comparison with the authentic compounds.

  DOI：

  10.1134/s1068162013030084
• 作为产物：
  描述：

  1-羟基苯并三唑 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以92%的产率得到1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)benzotriazole
  参考文献：
  名称：

  Glycosylated derivatives of substituted hydroxylamine. II. The phase transfer synthesis and the study of the glycosyl transfer reaction of glucosaminides of substituted hydroxylamine

  摘要：

  The interaction of 1-(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyloxy)benzotriazole with primary and secondary aliphatic and cycloaliphatic alcohols or diisopropylidenegalactose in refluxing methylene chloride under the catalysis of Lewis acids resulted in alkyl-O-glucosaminides with the 1,2-trans-configuration of the glycoside bond. Other glucosaminides of substituted hydroxylamine were shown not to react under these conditions. The structures of the synthesized glucosaminides were confirmed by H-1 NMR spectroscopy and comparison with the authentic compounds.

  DOI：

  10.1134/s1068162013030084