N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide | 522634-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide
• CAS: 522634-59-9
• 化学式: C₆₆H₇₅N₅O₁₅
• 分子量: 1178.35
• InChiKey: OMYBITIDIMXPDV-RJDJRJIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  86.0
• 可旋转键数：
  30.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  245.64
• 氢给体数：
  5.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 40.0 ℃ 、3.5 MPa 条件下， 反应 15.0h， 以95%的产率得到N-{2-acetamido-4-O-[3-[[(2-acetamido-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-2-deoxy-β-D-glucopyranosyl}-3-aminopropanoic acid amide
  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-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylamine 在 palladium on activated charcoal 、 三乙胺 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 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.58h， 生成 N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide
  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