2-cyanoethyl-(2-(2-(2-(thioacetyl)ethoxy)ethoxy)ethyl)-N,N-diisopropylphosphoramidite | 153870-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 2-cyanoethyl-(2-(2-(2-(thioacetyl)ethoxy)ethoxy)ethyl)-N,N-diisopropylphosphoramidite
• 英文别名: S-[2-[2-[2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyethoxy]ethoxy]ethyl] ethanethioate
• CAS: 153870-21-4
• 化学式: C₁₇H₃₃N₂O₅PS
• 分子量: 408.499
• InChiKey: FMIVUFGXNQLSTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5’-(4,4’-二甲氧基三苯基)-3’-脱氧胸苷 2’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 、 2-cyanoethyl-(2-(2-(2-(thioacetyl)ethoxy)ethoxy)ethyl)-N,N-diisopropylphosphoramidite 生成
  参考文献：
  名称：

  A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides

  摘要：

  A novel procedure is described for the introduction of a masked thiol function at the 5'-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. Our strategy is elaborated for oligothymidylates and is further illustrated for oligodeoxynucleotides which are base-protected with the 2-(acetoxymethyl)benzoyl group. Rapid base-deprotection can be accomplished in methanolic potassium carbonate which also effects saponification of the thioacetyl ester. The resultant free thiol is reacted in situ with dithiodipyridine to afford pyridyldisulfide-derivatized oligodeoxynucleotides.

  DOI：

  10.1016/s0040-4020(01)80247-7
• 作为产物：
  描述：

  三乙二醇单对甲苯磺酸酯 在 二异丙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 2-cyanoethyl-(2-(2-(2-(thioacetyl)ethoxy)ethoxy)ethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides

  摘要：

  A novel procedure is described for the introduction of a masked thiol function at the 5'-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. Our strategy is elaborated for oligothymidylates and is further illustrated for oligodeoxynucleotides which are base-protected with the 2-(acetoxymethyl)benzoyl group. Rapid base-deprotection can be accomplished in methanolic potassium carbonate which also effects saponification of the thioacetyl ester. The resultant free thiol is reacted in situ with dithiodipyridine to afford pyridyldisulfide-derivatized oligodeoxynucleotides.

  DOI：

  10.1016/s0040-4020(01)80247-7

文献信息

• A new strategy for the solid-phase synthesis of 5′-thiolated oligodeoxynucleotides
  作者：Will H.A. Kuijpers、Constant A.A. van Boeckel

  DOI：10.1016/s0040-4020(01)80247-7

  日期：1993.1

  A novel procedure is described for the introduction of a masked thiol function at the 5'-terminus of oligodeoxynucleotides. An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleotides using standard solid-phase techniques. Our strategy is elaborated for oligothymidylates and is further illustrated for oligodeoxynucleotides which are base-protected with the 2-(acetoxymethyl)benzoyl group. Rapid base-deprotection can be accomplished in methanolic potassium carbonate which also effects saponification of the thioacetyl ester. The resultant free thiol is reacted in situ with dithiodipyridine to afford pyridyldisulfide-derivatized oligodeoxynucleotides.