5’-O-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl (2-cyanoethyl) H-phosphonate | 1428553-39-2

• 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-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl (2-cyanoethyl) H-phosphonate
• CAS: 1428553-39-2
• 化学式: C₃₇H₄₄N₃O₈PSi
• 分子量: 717.831
• InChiKey: QSIOWWHUWYXXSW-DWNQJFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  141.87
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5’-O-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl (2-cyanoethyl) H-phosphonate 、 三乙胺 以 乙腈 为溶剂， 反应 0.08h， 以51%的产率得到triethylammonium 5’-O-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl H-phosphonate
  参考文献：
  名称：

  A BH3 masked H-phosphonate for coupling in oligonucleotide synthesis

  摘要：

  A method of masking 3'-H-phosphonate group for the solution-phase synthesis of ribonucleotide by H-phosphonate approach was described. The phosphonic acid group was masked by bis-(2-cyanoethyl) boranophosphate during the reactions. After a successive demasking treatment by triethylamine, trityl cation, and triethylamine, the triethylammonium 3'-H-phosphonate nucleotide can be obtained efficiently ready for the coupling cycle in synthesis of oligonucleotide. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.02.054
• 作为产物：
  描述：

  5’-O-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl bis-(2-cyanoethyl)boranophosphate 在 二氯乙酸 、 4,4’,4’-三甲氧基苯基甲醇 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.42h， 生成 5’-O-trityl-2’-tertbutyldimethylsilyl-uridin-3’-yl (2-cyanoethyl) H-phosphonate
  参考文献：
  名称：

  A BH3 masked H-phosphonate for coupling in oligonucleotide synthesis

  摘要：

  A method of masking 3'-H-phosphonate group for the solution-phase synthesis of ribonucleotide by H-phosphonate approach was described. The phosphonic acid group was masked by bis-(2-cyanoethyl) boranophosphate during the reactions. After a successive demasking treatment by triethylamine, trityl cation, and triethylamine, the triethylammonium 3'-H-phosphonate nucleotide can be obtained efficiently ready for the coupling cycle in synthesis of oligonucleotide. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.02.054