O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine | 113195-69-0

• 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: O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine
• 英文别名: O⁶-diphenylcarbamoyl-N²-phenylacetyl-2'-deoxyguanosine
• CAS: 113195-69-0
• 化学式: C₃₁H₂₈N₆O₆
• 分子量: 580.6
• InChiKey: UPKCXWFYOYFJBI-BFLUCZKCSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  151.93
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine 在 吡啶 、 bis(2-oxo-3-oxazolidinyl)phosphoric acid chloride 、 N,N-二异丙基乙胺 、 3-硝基-1,2,4-三氮唑 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 tributylammonium 5'-O-dimethoxytrityl-O⁶-diphenylcarbamoyl-N²-phenylacetyl-2'-deoxyguanosin-3'-yl methyl boranophosphate
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875
• 作为产物：
  描述：

  N²-Phenylacetyl-2'-deoxyguanosine 、 二苯氨基甲酰氯 在 六甲基二硅氮烷 、 吡啶 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以87%的产率得到O6-diphenylcarbamoyl-N2-phenylacetyl-2'-deoxyguanosine
  参考文献：
  名称：

  A Novel Method for the Synthesis of Dinucleoside Boranophosphates by a Boranophosphotriester Method

  摘要：

  2'-Deoxyribonucleoside-3'-boranophosphates (nucleotide monomers), including four kinds of nucleobases, were synthesized in good yields by the use of new boranophosphorylating reagents. We have explored various kinds of condensing reagents as well as nucleophilic catalysts for the boranophosphorylation reaction with nucleosides. In the synthesis of dinucleoside boranophosphates, undesirable side reactions occurred at the O-4 of thymine and the O-6 of N-2-phenylacetylguanine bases. To avoid these side reactions, additional protecting groups, benzoyl (Bz) and diphenylcarbamoyl (Dpc) groups, were introduced to thymine and guanine bases, respectively. As a result, the condensation reactions proceeded smoothly without any side reactions, and the dimers including four kinds of nucleobases were obtained in excellent yields. In the deprotection of the 5'-DMTr group, Et3SiH was found to be effective as a scavenger for the DMTr cation which caused a P-B bond cleavage. After removal of the other protecting groups by the conventional procedure, four kinds of dinucleoside boranophosphates were obtained in good yields.

  DOI：

  10.1021/jo0493875