N-[o-(benzimidazol-2-yl)phenyl]-α-,β-D-xylopyranosylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-[o-(benzimidazol-2-yl)phenyl]-α-,β-D-xylopyranosylamine
• 英文别名: (3R,4S,5R)-2-[2-(1H-benzimidazol-2-yl)anilino]oxane-3,4,5-triol
• 化学式: C₁₈H₁₉N₃O₄
• 分子量: 341.367
• InChiKey: AJQLBGFUKVKCTG-INYHJIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-吡喃木糖 、 2-(2-氨基苯基)苯并咪唑 以 乙醇 为溶剂， 反应 0.25h， 以69%的产率得到N-[o-(benzimidazol-2-yl)phenyl]-α-,β-D-xylopyranosylamine
  参考文献：
  名称：

  Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-d-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses

  摘要：

  Twelve N-glycosyl amines were synthesised using 4,6-O-benzylidene-D-glucopyranose and different substituted aromatic amines, including some diamines that resulted in bis-glycosyl amines. Another set of six N-glycosyl amines was synthesised using different hexoses and pentoses and 2-(o-aminophenyl)benzimidazole. All compounds were isolated as solid products and purified, their elemental compositions were established, and these were characterised by NMR (H-1 and C-13), UV-Vis, and FTIR spectroscopy, by FAB mass spectrometry (molecular-ion peaks gave molecular weights), and by their optical rotations. While the protected saccharide, 4,6-O-benzylidene-D-glucopyranose, exists as a mixture of P and a anomers in solution, the corresponding N-glycosyl amines were of only the P anomeric form as determined by NMR and FTIR spectroscopy. On the other hand, N-glycosyl amines synthesised from 2-(o-aminophenyl)benzimidazole prefer the a anomeric form, and in two cases a mixture of both the P and the alpha anomers were observed. The trends observed in the chemical shifts were compared among different products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00202-6

文献信息

• Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-d-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses
  作者：T.Mohan Das、Chebrolu P Rao、Erkki Kolehmainen

  DOI：10.1016/s0008-6215(01)00202-6

  日期：2001.9

  Twelve N-glycosyl amines were synthesised using 4,6-O-benzylidene-D-glucopyranose and different substituted aromatic amines, including some diamines that resulted in bis-glycosyl amines. Another set of six N-glycosyl amines was synthesised using different hexoses and pentoses and 2-(o-aminophenyl)benzimidazole. All compounds were isolated as solid products and purified, their elemental compositions were established, and these were characterised by NMR (H-1 and C-13), UV-Vis, and FTIR spectroscopy, by FAB mass spectrometry (molecular-ion peaks gave molecular weights), and by their optical rotations. While the protected saccharide, 4,6-O-benzylidene-D-glucopyranose, exists as a mixture of P and a anomers in solution, the corresponding N-glycosyl amines were of only the P anomeric form as determined by NMR and FTIR spectroscopy. On the other hand, N-glycosyl amines synthesised from 2-(o-aminophenyl)benzimidazole prefer the a anomeric form, and in two cases a mixture of both the P and the alpha anomers were observed. The trends observed in the chemical shifts were compared among different products. (C) 2001 Elsevier Science Ltd. All rights reserved.