2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol | 191097-75-3

• 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: 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
• CAS: 191097-75-3
• 化学式: C₄₂H₄₀N₂O₅
• 分子量: 652.79
• InChiKey: XXEGSZFOCXNUQV-FLDZOFIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.28
• 重原子数：
  49.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.83
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 palladium on activated charcoal 氢气 、 吡啶 作用下， 以 甲酸 、 溶剂黄146 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 63.0h， 以76%的产率得到1,3,4,5-tetra-O-acetyl-7-[2-(1-acetyl)benzimidazolyl]-2,6-anhydro-7-deoxy-L-glycero-L-gulo-heptitol
  参考文献：
  名称：

  Synthesis and Reactions ofC-Hetaryl Substituted Ketoses

  摘要：

  O-Benzyl protected gluconolactone 1 reacts readily with 2-lithio derivatives of quinaldine, 2-methylquinoxaline, 2-methylbenzimidazole and N-protected derivatives, and 1-benzyloxymethyl-2-methylimidazole at low temperatures to afford as monoaddition products the corresponding D-gluco-2-heptuloses 2-5. The benzyl protective groups can be readily removed by hydrogenolysis as shown for the transformation of 4a into 8. Acylation reactions with 4a exhibited an interesting interplay between O- and N-acylation which is dependent on the nature of the acylating agent and on the reaction conditions. Reductive removal of the anomeric hydroxy group in 4a-c and 5 was readily performed via elimination products 18a-c and 23; their hydrogenation with Pd/C gave directly the O,N-deprotected C-beta-D-glucopyranosylmethyl derivatives 21 and 25, respectively.

  DOI：

  10.1080/07328309708006530
• 作为产物：
  描述：

  1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-2-heptulopyranose 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以35%的产率得到2,6-anhydro-1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
  参考文献：
  名称：

  Synthesis and Reactions ofC-Hetaryl Substituted Ketoses

  摘要：

  O-Benzyl protected gluconolactone 1 reacts readily with 2-lithio derivatives of quinaldine, 2-methylquinoxaline, 2-methylbenzimidazole and N-protected derivatives, and 1-benzyloxymethyl-2-methylimidazole at low temperatures to afford as monoaddition products the corresponding D-gluco-2-heptuloses 2-5. The benzyl protective groups can be readily removed by hydrogenolysis as shown for the transformation of 4a into 8. Acylation reactions with 4a exhibited an interesting interplay between O- and N-acylation which is dependent on the nature of the acylating agent and on the reaction conditions. Reductive removal of the anomeric hydroxy group in 4a-c and 5 was readily performed via elimination products 18a-c and 23; their hydrogenation with Pd/C gave directly the O,N-deprotected C-beta-D-glucopyranosylmethyl derivatives 21 and 25, respectively.

  DOI：

  10.1080/07328309708006530