文献类型：期刊文献

英文题名：DIVERSITY-ORIENTED SYNTHESIS OF 2-SUBSTITUTED PURINE NUCLEOSIDES FROM AVAILABLE NUCLEOSIDES VIA THE LATE-STAGE NITRATION/DERIVATIZATION

作者：Xia, Ran[1];Liu, Li-Jie[1];Xia, Chao[1];Sun, Li -Ping[2];Chen, Lei -Shan[2]

通讯作者：Xia, R[1];Chen, LS[2]

机构：[1]Xinxiang Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China;[2]Xinxiang Univ, Sch Life Sci & Basic Med, Xinxiang 453003, Henan, Peoples R China

第一机构：新乡学院

通讯机构：[1]corresponding author), Xinxiang Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China;[2]corresponding author), Xinxiang Univ, Sch Life Sci & Basic Med, Xinxiang 453003, Henan, Peoples R China.|[11071]新乡学院;

年份：2022

卷号：104

期号：8

起止页码：1447-1460

外文期刊名：HETEROCYCLES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000835343100005)，CCR-EXPANDED(收录号:WOS:000835343100005)】；

基金：We thank the Key Scientific and Technical Projects of Henan Province (212102310333, 222102110403) , the Training Plan for Young Key Teachers in Universities of Henan Province (202GGJS248) , the Key Scientific and Technical Projects of Xinxiang City (GG2021016) and the Major Scientific and Technical Projects of Xinxiang City (21ZD008) for financial support.

语种：英文

摘要：A practical synthesis of 2-substituted purine nucleosides was developed in good to excellent yields from readily available nucleosides, such as adenosine, vidarabine and 2 '-deoxyadenosine, via the late-stage nitration/derivatization. The C(2)-H bonds of purines were nitrated by 2,2,2-trifluoroacetic anhydride/Bu4NNO3, followed by nucleophilic substitution or hydrogenolysis reduction converting C(2)-NO2 to C(2)-Cl, C(2)-F, C(2)-N, C(2)-O and C(2)-S bonds. This system could tolerate arabinofuranosyl, ribosyl, deoxyribosyl,-OH or -NH2 groups. The clinical drugs, Regadenoson, Cladribine and Fludarabine, and the important naturally occurring nucleosides, spongosine and crotonoside, could be obtained successfully even on 20 g scales, which made this route more attractive for industrial applications.