Seven-membered cyclic phosphate: synthesis and properties of S-cycloadenosine 2′ 5′-cyclic phosphate and cordycepin 2′, 5′-cyclic phosphate. Studies of nucleosides and nucleotides. LXIV′l). Purine cyclonucleosides 25.

摘要

8,3′-Anhydro-8-mercapto-9-β-D-xylofuranosyladenine (8,3′-S-cycloadenosine) was phosphorylated with cyanoethyl phosphate and DCC to 5′-phosphate. After 6-amino group was benzoylated, the monophosphate was treated with DCC to give a cyclic phosphate (II). The structure of compound II was elucidated as 8,3′-S-cycloadenosine 2′,5′-cyclic phosphate by UV, NMR and CD spectra, as well as enzymatic hydrolyses. When compound II was desulfurized with Raney nickel, cordycepin 2′,5′-cyclic phosphate (III) was obtained. Although compound III could be obtained from cordycepin 5′-phosphate with DCC, the yield was extremely low.