O⁶,7-Dibenzylguanine

• 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: O⁶,7-Dibenzylguanine
• 英文别名: 7-Benzyl-6-benzyloxy-7h-purin-2-ylamine；7-benzyl-6-phenylmethoxypurin-2-amine
• 化学式: C₁₉H₁₇N₅O
• 分子量: 331.377
• InChiKey: ZNVQFYXIYWGAJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2'-脱氧鸟苷 在 sodium hydroxide 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 144.0h， 生成 O⁶,7-Dibenzylguanine
  参考文献：
  名称：

  Effect of Ionic State of 2‘-Deoxyguanosine and Solvent on Its Aralkylation by Benzyl Bromide

  摘要：

  To extend studies of the aralkylation of nucleic acid components under a variety of solvent conditions, we determined product distributions from the reactions of benzyl bromide with 2'-deoxyguanosine and the anion of 2'-deoxyguanosine in 2,2,2-trifluoroethanol (TFE) and compared these distributions with those from the reaction of the anion with benzyl bromide in N'\N-dimethylacetamide (DMA). 7-Benzylguanine was the only benzylated product detected in the reaction with the neutral nucleoside in TFE, In striking contrast, the reaction of the anion of 2'-deoxyguanosine with benzyl bromide in TFE produced N-2-benzyl-2'-deoxyguanasine in significant yield and with high selectivity. The reaction of the anion of 2'-deoxyguanosine with benzyl bromide in DMA produced products derived only from reaction at the 1- and/or 7-position of the nucleoside. The weakly nucleophilic but protic polar solvent TFE and the iminolate tautomeric form of the 2'-deoxyguanosine anion appear to be essential for benzylation at the exocyclic N-2-position.

  DOI：

  10.1021/tx980012m

文献信息

• Convenient synthesis of 2,9-disubstituted guanines mediated by solid-supported reagents
  作者：Warren McComas、Li Chen、Kyungjin Kim

  DOI：10.1016/s0040-4039(00)00466-4

  日期：2000.5

  A novel application has been developed to separate regioisomers chemoselectively using a solid-supported reagent. An N7/N9 purine regioisomer mixture was purified using aluminum oxide/H+ to provide the N9 isomer selectively as a parallel or high-throughput format (chemoselective high-throughput purification). 2,9-Disubstituted guanines were conveniently prepared by this new method in conjunction with solid-supported reagents. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Effect of Ionic State of 2‘-Deoxyguanosine and Solvent on Its Aralkylation by Benzyl Bromide
  作者：Ki-Young Moon、Robert C. Moschel

  DOI：10.1021/tx980012m

  日期：1998.6.1

  To extend studies of the aralkylation of nucleic acid components under a variety of solvent conditions, we determined product distributions from the reactions of benzyl bromide with 2'-deoxyguanosine and the anion of 2'-deoxyguanosine in 2,2,2-trifluoroethanol (TFE) and compared these distributions with those from the reaction of the anion with benzyl bromide in N'\N-dimethylacetamide (DMA). 7-Benzylguanine was the only benzylated product detected in the reaction with the neutral nucleoside in TFE, In striking contrast, the reaction of the anion of 2'-deoxyguanosine with benzyl bromide in TFE produced N-2-benzyl-2'-deoxyguanasine in significant yield and with high selectivity. The reaction of the anion of 2'-deoxyguanosine with benzyl bromide in DMA produced products derived only from reaction at the 1- and/or 7-position of the nucleoside. The weakly nucleophilic but protic polar solvent TFE and the iminolate tautomeric form of the 2'-deoxyguanosine anion appear to be essential for benzylation at the exocyclic N-2-position.