N-(9H-purine-6-yl)-2,2,3,3-tetramethylsuccinimide | 1202405-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-(9H-purine-6-yl)-2,2,3,3-tetramethylsuccinimide
• 英文别名: 3,3,4,4-tetramethyl-1-(7H-purin-6-yl)pyrrolidine-2,5-dione
• CAS: 1202405-91-1
• 化学式: C₁₃H₁₅N₅O₂
• 分子量: 273.294
• InChiKey: MSFZYWMFYJPEFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(9H-purine-6-yl)-2,2,3,3-tetramethylsuccinimide 、 1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 三(3,6-二氧杂庚基)胺 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以71%的产率得到9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
  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：

  3,3,4,4-四甲基四氢呋喃-2,5-二酮 、 腺嘌呤 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 氯化亚砜 作用下， 反应 22.0h， 以78%的产率得到N-(9H-purine-6-yl)-2,2,3,3-tetramethylsuccinimide
  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