acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside | 191097-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside
• CAS: 191097-79-7
• 化学式: C₅₂H₅₂N₂O₈
• 分子量: 832.993
• InChiKey: VTONJZAXVCNWTA-WYCSEUNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.38
• 重原子数：
  62.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以69%的产率得到2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)benzimidazolyl]-1-deoxy-D-gluco-hept-2-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
• 作为产物：
  描述：

  1-benzyloxymethyl-2-methylbenzimidazole 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 acetyl-3,4,5,7-tetra-O-benzyl-1-[2-(1-benzyloxymethyl)benzimidazolyl]-1-deoxy-α-D-gluco-2-heptulopyranoside
  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