3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose | 191097-71-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose
• CAS: 191097-71-9
• 化学式: C₄₄H₄₄N₂O₈
• 分子量: 728.842
• InChiKey: MEGAUHXAUWUGSD-CASATDKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  110.5
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到1-(2-benzimidazolyl)-3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-methyloxycarbonyl-α-D-gluco-2-heptulopyranose
  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：

  5-内酯 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 3,4,5,7-tetra-O-benzyl-1-deoxy-1-[2-(1-methyloxycarbonyl)benzimidazolyl]-α-D-gluco-2-heptulopyranose
  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