N,N'-(9H-purine-2,6-diyl)bis(2,2,3,3-tetramethylsuccinimide) | 1212821-89-0

• 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,N'-(9H-purine-2,6-diyl)bis(2,2,3,3-tetramethylsuccinimide)
• 英文别名: 3,3,4,4-tetramethyl-1-[2-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)-7H-purin-6-yl]pyrrolidine-2,5-dione
• CAS: 1212821-89-0
• 化学式: C₂₁H₂₆N₆O₄
• 分子量: 426.475
• InChiKey: JRVVNVVEUNKXIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride 、 N,N'-(9H-purine-2,6-diyl)bis(2,2,3,3-tetramethylsuccinimide) 在 sodium hydride 作用下， 以 乙腈 、 mineral oil 为溶剂， 反应 13.0h， 以93%的产率得到9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-2,6-di-(3,3,4,4-tetramethyl-2,5-dioxopyrrolidin-1-yl)purine
  参考文献：
  名称：

  Preparation of the 2′-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation

  摘要：

  The purine nucleoside 2,6-diamonopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diamonopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O-2-carbonyl with TMSCl, the N-6-amino groups is protected as the tetramethylsuccinimide (M4SI). The O-2-carbonyl is protected as the DPC derivative, and the trityl groups is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.

  DOI：

  10.1021/jo902616s
• 作为产物：
  描述：

  3,3,4,4-四甲基四氢呋喃-2,5-二酮 、 2,6-二氨基嘌呤 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 30.0h， 以74%的产率得到N,N'-(9H-purine-2,6-diyl)bis(2,2,3,3-tetramethylsuccinimide)
  参考文献：
  名称：

  Preparation of the 2′-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation

  摘要：

  The purine nucleoside 2,6-diamonopurine-2'-deoxyriboside is prepared by the direct glycosylation of the 2,6-bis(tetramethylsuccinimide) derivative of the parent purine heterocycle 4 with 2-deoxy-3,5-di-O-(p-toluoyl)-alpha-D-erythro-pentofuranosyl chloride 5 using the sodium salt method. 2'-Deoxyisoguanosine is prepared from 2,6-diaminopurine by a five-step procedure. The purine heterocycle isoguanine is prepared by selective diazotization of 2,6-diamonopurine and then converted to the N9-trityl derivative to increase solubility. After silylation of the O-2-carbonyl with TMSCl, the N-6-amino groups is protected as the tetramethylsuccinimide (M4SI). The O-2-carbonyl is protected as the DPC derivative, and the trityl groups is removed. The resulting product is glycosylated in good yield to generate fully protected 2'-deoxyisoguanosine.

  DOI：

  10.1021/jo902616s