1-[2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine | 1202405-99-9

• 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: 1-[2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine
• CAS: 1202405-99-9
• 化学式: C₂₀H₂₆N₄O₅
• 分子量: 402.45
• InChiKey: OBQQXIOJJMVDIQ-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117.78
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-[2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 3.0h， 以87%的产率得到1-[5'-O-(4,4'-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations

  摘要：

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.

  DOI：

  10.1021/ol9025028
• 作为产物：
  描述：

  1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以82%的产率得到1-[2-deoxy-β-D-erythro-pentofuranosyl]-4-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7-methyl-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  Tetramethylsuccinimide as a Directing/Protecting Group in Purine Glycosylations

  摘要：

  Tetra methylsuccinic anhydride can be used to protect the exocyclic amine of 6-aminopurine derivatives by forming the corresponding tetramethysuccinimide. X-ray crystallography confirms that the imide carbonyl and the methyl groups are positioned to sterically block the N7 nitrogen so that glycosylations occur with very high regiochemical control at N9. This approach Is particularly effective for 3-substituted purines where the substituent tends to block access to N9 and inhibit glycosylation at that site.

  DOI：

  10.1021/ol9025028