N-benzoyldeoxyadenosine 5'-(3'',5''-dimethoxybenzoin)carbonate | 167872-05-1

• 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: N-benzoyldeoxyadenosine 5'-(3'',5''-dimethoxybenzoin)carbonate
• 英文别名: [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl [1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethyl] carbonate
• CAS: 167872-05-1
• 化学式: C₃₄H₃₁N₅O₉
• 分子量: 653.648
• InChiKey: RRMYCASRJCVYHJ-FROGWBQUSA-N

物化性质

• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-benzoyldeoxyadenosine 5'-(3'',5''-dimethoxybenzoin)carbonate 以 苯 为溶剂， 反应 1.0h， 以97%的产率得到N-苯甲酰基-2’-脱氧腺苷
  参考文献：
  名称：

  Dimethoxybenzoin Carbonates: Photochemically-Removable Alcohol Protecting Groups Suitable for Phosphoramidite-Based DNA Synthesis

  摘要：

  DOI：

  10.1021/jo00110a011
• 作为产物：
  描述：

  3,5-dimethoxybenzoin 在 吡啶 作用下， 以 硝基甲烷 为溶剂， 反应 2.0h， 生成 N-benzoyldeoxyadenosine 5'-(3'',5''-dimethoxybenzoin)carbonate
  参考文献：
  名称：

  Dimethoxybenzoin Carbonates: Photochemically-Removable Alcohol Protecting Groups Suitable for Phosphoramidite-Based DNA Synthesis

  摘要：

  DOI：

  10.1021/jo00110a011

文献信息

• Comparison of Methods for Photochemical Phosphoramidite-Based DNA Synthesis
  作者：Michael C. Pirrung、Jean-Claude Bradley

  DOI：10.1021/jo00125a010

  日期：1995.10

  Toward the goal of preparing surface-bound arrays of short oligonucleotides using light-directed synthesis, we have studied novel photoremovable protecting groups for solid-phase DNA synthesis. We have protected the 5'-hydroxyls of all four nucleosides with our recently-described 3',5'-dimethoxybenzoin carbonate (DMB-carbonate) group and converted the products to (cyanoethyl)phosphoramidites. For comparison with another recently-described method for photochemical DNA synthesis, we have prepared the methylnitropiperonyl carbonate (MeNPOC) derivative of thymidine and its amidite. To permit chain attachment to supports, the thymidine DMB-carbonate succinoyl derivative was also prepared. High cycle yields (based on release of the photoproduct dimethoxyphenylbenzofuran) were obtained in initial photochemical DNA synthesis studies with DMB-carbonates. An increase in the deprotection half-life was seen with increasing oligomer length, but this effect was scale-dependent and should be minimal at the small scale at which most DNA arrays will be prepared. The oligonucleotides resulting from these syntheses contained some impurities. It was shown that 350 nm irradiation does not produce thymine dimers but does damage benzoylcytidine. This problem is solved through a change of protecting groups. However, other factors also affect the quality of the DNA prepared by photochemical synthesis, since direct comparisons between short oligomers of thymine prepared with DMTr, DMB-carbonate, and MeNPOC protecting groups show that photochemical deprotection results in diminished cycle yields compared to acid deprotection.
• Dimethoxybenzoin Carbonates: Photochemically-Removable Alcohol Protecting Groups Suitable for Phosphoramidite-Based DNA Synthesis
  作者：Michael C. Pirrung、Jean-Claude Bradley

  DOI：10.1021/jo00110a011

  日期：1995.3