Studies on trifluoromethylphosphonamidite analogues as building blocks in oligonucleotide synthesis
摘要:
The phosphorylating reagents CF3P(NMe(2))Cl and CF3P(NEt(2))Cl are used to phosphorylate the 3'-hydroxyl moiety of several protected 2'-deoxynucleosides yielding the corresponding nucleoside trifluoromethyl phosphonamidites. Their scope and limitations towards amidite activation are investigated but, however, their behavior is completely different to commonly used nucleoside phosphorus amidites.
本文描述了具有至少一个吸电子五氟乙基的不对称取代的次膦酸和氧化膦的合成。二乙氨基官能团作为保护基团的存在允许RC1PNEt 2(R = CF 3,C 6 F 5,C 6 H 5)与LiC 2 F 5选择性反应。经对甲苯磺酸处理后,分离出的氨基膦R(C 2 F 5)PNEt 2它们容易分别转化为相应的亚膦酸或氧化膦。氧化物和酸互变异构体之间的互变异构平衡研究表明,(CF 3)(C 2 F 5)POH为稳定的次膦酸,而五氟苯基和苯基衍生物构成了酸和氧化物互变异构体之间的溶剂依赖性平衡。