文献类型：期刊文献

英文题名：Synthesis of 2 '-deoxyguanosine from 2 '-deoxyadenosine via C2 nitration

作者：Xia, Ran[1];Chen, Lei-Shan[2];Xu, Shao-Hong[1];Xia, Chao[1];Sun, Li-Ping[2]

通讯作者：Xia, R[1];Sun, LP[2]

机构：[1]Xinxiang Univ, Sch Pharm, Xinxiang, Henan, Peoples R China;[2]Xinxiang Univ, Sch Life Sci & Basic Med, Xinxiang, Henan, Peoples R China

第一机构：新乡学院

通讯机构：[1]corresponding author), Xinxiang Univ, Sch Pharm, Xinxiang, Henan, Peoples R China;[2]corresponding author), Xinxiang Univ, Sch Life Sci & Basic Med, Xinxiang, Henan, Peoples R China.|[11071]新乡学院;

年份：0

外文期刊名：NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000779620200001)，CCR-EXPANDED(收录号:WOS:000779620200001)】；

基金：We thank the National Natural Science Foundation of China (21602189), the Key Scientific and Technical Projects of Henan Province (212102310333) and the Training Plan for young Key Teachers in Universities of Henan Province (2020GGJS248) for financial support.

语种：英文

摘要：An efficient synthetic method has been developed for the synthesis of 2 '-deoxyguanosine from the more commercially available 2 '-deoxyadenosine via late-stage C2 nitration in 48.7% total yield by a 5-step synthetic procedure. Crucially, 2 '-deoxyadenosine was fully protected by bennzoyl groups and then nitrated at C2 by tetrabutylammonium nitrate/trifluoroacetic anhydride. The resulting 2-NO2 moiety was converted into 2-NH2 by Ni-catalyzed hydrogenolysis. Finally, 2 '-deoxyguanosine was obtained from the diaminopurine intermediate by deaminase-catalyzed reaction. Furthermore, the 2-NO2 moiety also appeared to be a versatile handle to introduce a variety of functional groups, resulting in a divergent access to 2-substituted 2 '-deoxyadenosine analogues.