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 | 1202405-98-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 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
• CAS: 1202405-98-8
• 化学式: C₃₄H₃₅N₅O₇
• 分子量: 625.681
• InChiKey: GILGPOJJVNSFIO-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142.81
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  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 在 甲醇 、 sodium methylate 作用下， 反应 8.0h， 以64%的产率得到9-[2-deoxy-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：

  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