(2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl bis(2-cyanoethyl) phosphite | 1428553-45-0

• 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: (2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl bis(2-cyanoethyl) phosphite
• CAS: 1428553-45-0
• 化学式: C₄₀H₄₇N₄O₈PSi
• 分子量: 770.894
• InChiKey: YDHPVPALFGTYAA-UMHCDNJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  54.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  157.82
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl bis(2-cyanoethyl) phosphite 在 二氯乙酸 、 硼烷四氢呋喃络合物 、 4,4’,4’-三甲氧基苯基甲醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 0.92h， 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
• 作为产物：
  描述：

  2’-O-(叔-丁基二甲基硅烷基)-5’-O-三苯甲基尿苷 、 3-羟基丙腈 在 2,6-二甲基吡啶 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.41h， 生成 (2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-((trityloxy)methyl)tetrahydrofuran-3-yl bis(2-cyanoethyl) phosphite
  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