The Total Synthesis Of Puromycin And Its Analogues

Puromycin and its analogues have been deeply studied and widely used in pharmacy, biochemistry, medicine and many other fields of life science frontier because of their antiviral, antitumor, antibacterial, immune suppression, and other significant biological activity. Therefore, design and synthesis of these compounds are of important significance.In this paper, a series of purine nucleoside analogues with significant natural activity have been synthesized, such as puromycin, cystocin, 9-[3’-Deoxy-3’-N-(L-phenylalany)amido-β-D-ribofuranosyl]adenine,9-[3’-Deoxy-3’-amido-β-D-ribofuranosyl]-9H-adenine, using Vorbruggen glycosylation reaction.The critical steps in the synthesis of these nucleoside derivatives are the coupling reaction of ribose derivatives with the base in Vorbruggen glycosylation conditions, deprotection in the ammonia-alcohol solution, the reduction of 3’-azido group in nucleoside compounds, coupling with another amino acid reagent, removal of the protecting group on the amino purine nucleoside.Vorbruggen glycosylation is a better route for the synthesis of these nucleoside analogues, giving ideal yields. This whole route is the advantage of cheap and accessible raw materials, high yield.