472965-94-9Relevant academic research and scientific papers
Synthesis and anti-HIV activity of β-D-3′-azido-2′, 3′-unsaturated nucleosides and β-D-3′-azido-3′- deoxyribofuranosylnucleosides
Gadthula, Srinivas,Chu, Chung K.,Schinazi, Raymond F.
, p. 1707 - 1727 (2007/10/03)
□ Since the discovery of 3′-azido-3′-deoxythymidine (AZT) and 2′,3′-didehydro-2prime;,3′-dideoxythymidine (d4T) as potent and selective inhibitors of the replication of human immunodeficiency virus (HIV), there has been a growing interest for the synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides with electron withdrawing groups on the sugar moiety. Here we described an efficient method for the synthesis of such nucleoside analogs bearing structural features of both AZT and d4T. The hey intermediate, 3-azido-1,2-bis-O-acetyl-5-O-benzoyl-3- deoxy-D-ribofuranose, 5 was synthesized from commercially available D-xylose in five steps, from which a series of pyrimidine and purine nucleosides were synthesized in high yields. The resultant protected nucleosides were converted to target nucleosides using appropriate chemical modifications. The final nucleosides were evaluated as potential anti-HIV agents. Copyright Taylor & Francis Group, LLC.
