2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide | 522634-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide
• CAS: 522634-51-1
• 化学式: C₂₆H₃₀N₄O₈
• 分子量: 526.546
• InChiKey: XADHRXPPWMUFBL-VKQKEIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  169.15
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide 在 palladium dihydroxide 、 palladium on activated charcoal 、 三乙胺 盐酸 、 4 A molecular sieve 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 35.58h， 生成 2-acetamido-4-O-[3-[[(2-acetamido-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  SYNTHESIS AND CONFORMATIONAL ANALYSIS OF PSEUDOSUGAR ANALOGUES OF CHITOTRIOSE 1*

  摘要：

  EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation afforded N,N"-diacetylpseudochitotriose 7. Coupling of 5 with heterocyclic or with Cbz protected aliphatic amino acids yielded glycosyl amides 8-12. Deprotection of 11 and 12 afforded the N,N'-diacetylpseudochitotriosyl amides of beta-alanine, 13, and L-arginine, 14. Molecular modelling calculations revealed that the pseudotrisaccharides exist in low energy extended conformations which show similar space filling as N,N',N"-triacetylchitotriose.

  DOI：

  10.1081/car-120016847
• 作为产物：
  描述：

  2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl azide 在 盐酸 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-acetamido-3,6-di-O-benzyl-4-O-succinoyl-2-deoxy-β-D-glucopyranosyl azide
  参考文献：
  名称：

  SYNTHESIS AND CONFORMATIONAL ANALYSIS OF PSEUDOSUGAR ANALOGUES OF CHITOTRIOSE 1*

  摘要：

  EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation afforded N,N"-diacetylpseudochitotriose 7. Coupling of 5 with heterocyclic or with Cbz protected aliphatic amino acids yielded glycosyl amides 8-12. Deprotection of 11 and 12 afforded the N,N'-diacetylpseudochitotriosyl amides of beta-alanine, 13, and L-arginine, 14. Molecular modelling calculations revealed that the pseudotrisaccharides exist in low energy extended conformations which show similar space filling as N,N',N"-triacetylchitotriose.

  DOI：

  10.1081/car-120016847