5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-O-Lev | 656249-30-8

• 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: 5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-O-Lev
• 英文别名: [(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphinothioyl]oxymethyl]-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate
• CAS: 656249-30-8
• 化学式: C₅₉H₆₂N₉O₁₅PS
• 分子量: 1200.23
• InChiKey: DUPWWUSPCKMWNU-BNJCRTMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  323
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-O-Lev 在 吡啶 、 Amberlyst 15 N₂H₅⁽¹⁺⁾ 、 溶剂黄146 作用下， 反应 4.0h， 以90%的产率得到5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-OH
  参考文献：
  名称：

  High-Yield Solution-Phase Synthesis of Di- and Trinucleotide Blocks Assisted by Polymer-Supported Reagents

  摘要：

  [GRAPHICS]A new solution-phase phosphoramidite approach is reported for oligonucleotide synthesis employing recyclable solid-supported reagents. It uses polyvinyl pyridinium tosylate as the activator of a nucleoside-3'-O-phosphoramidite in the coupling step with a 5'-OH nucleoside or dinucleotide. The resulting phosphite triester was either sulfurized or oxidized using polystyrene-bound trimethylammonium tetrathionate or periodiate. This method avoids complicated purification steps, as excess reagents are easily removed by filtration.

  DOI：

  10.1021/ol0511777
• 作为产物：
  描述：

  N²-isobutyryl-3'-O-levulinyl-2'-deoxyguanosine 、 5’-O-(4,4’-二甲氧基三苯基)-N4-苯甲酰基-2’-脱氧胞苷-3’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 poly(4-vinylpyridinium-p-toluenesulfonate) 、 水 、 吡啶 、 Amberlyst A-26 tetrathionate 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 5'-O-DMTr-dC^Bzps_CNEdG^i-Bu-3'-O-Lev 、 5'-O-(4,4'-dimethoxytrityl)N-benzoyl-cytosine-3'-O-(2-cyanoethyl) H-phosphonate
  参考文献：
  名称：

  High-Yield Solution-Phase Synthesis of Di- and Trinucleotide Blocks Assisted by Polymer-Supported Reagents

  摘要：

  [GRAPHICS]A new solution-phase phosphoramidite approach is reported for oligonucleotide synthesis employing recyclable solid-supported reagents. It uses polyvinyl pyridinium tosylate as the activator of a nucleoside-3'-O-phosphoramidite in the coupling step with a 5'-OH nucleoside or dinucleotide. The resulting phosphite triester was either sulfurized or oxidized using polystyrene-bound trimethylammonium tetrathionate or periodiate. This method avoids complicated purification steps, as excess reagents are easily removed by filtration.

  DOI：

  10.1021/ol0511777

文献信息

• High-Yield Solution-Phase Synthesis of Di- and Trinucleotide Blocks Assisted by Polymer-Supported Reagents
  作者：Cécile Dueymes、Andreas Schönberger、Ilaria Adamo、Aude-Emmanuelle Navarro、Albert Meyer、Meinolf Lange、Jean-Louis Imbach、Fritz Link、François Morvan、Jean-Jacques Vasseur

  DOI：10.1021/ol0511777

  日期：2005.8.1

  [GRAPHICS]A new solution-phase phosphoramidite approach is reported for oligonucleotide synthesis employing recyclable solid-supported reagents. It uses polyvinyl pyridinium tosylate as the activator of a nucleoside-3'-O-phosphoramidite in the coupling step with a 5'-OH nucleoside or dinucleotide. The resulting phosphite triester was either sulfurized or oxidized using polystyrene-bound trimethylammonium tetrathionate or periodiate. This method avoids complicated purification steps, as excess reagents are easily removed by filtration.