N-(2-oxo-9-trityl-2,9-dihydro-1H-purin-6-yl)-2,2,3,3-tetramethylsuccinimide | 1212821-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(2-oxo-9-trityl-2,9-dihydro-1H-purin-6-yl)-2,2,3,3-tetramethylsuccinimide
• 英文别名: 3,3,4,4-tetramethyl-1-(2-oxo-9-trityl-1H-purin-6-yl)pyrrolidine-2,5-dione
• CAS: 1212821-93-6
• 化学式: C₃₂H₂₉N₅O₃
• 分子量: 531.614
• InChiKey: JDPPQFCMRNOMRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  94.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-oxo-9-trityl-2,9-dihydro-1H-purin-6-yl)-2,2,3,3-tetramethylsuccinimide 、 二苯氨基甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 1.5h， 生成
  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 、 以 吡啶 为溶剂， 反应 12.0h， 以539 mg的产率得到N-(2-oxo-9-trityl-2,9-dihydro-1H-purin-6-yl)-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

文献信息

• Preparation of the 2′-Deoxynucleosides of 2,6-Diaminopurine and Isoguanine by Direct Glycosylation
  作者：Joseph W. Arico、Amy K. Calhoun、Larry W. McLaughlin

  DOI：10.1021/jo902616s

  日期：2010.3.5

  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.