Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 104, No. 8, 2022, pp.1447-1460
Published online, 20th June, 2022
DOI: 10.3987/COM-22-14689
Diversity-Oriented Synthesis of 2-Substituted Purine Nucleosides from Available Nucleosides via the Late-Stage Nitration/Derivatization

Ran Xia,* Li-Jie Liu, Chao Xia, Li-Ping Sun, and Lei-Shan Chen*

*Department of Chemistry and Chemical Engineering, Xinxiang University, East of JinSui Road, XinXiang City, Henan Province, 453003, China


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.