A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides XVI)

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Abstract
A versatile method for the synthesis of 5′-deoxy-8,5′-cycloadenosine, a conformationally-fixed “anti” type of adenosine, was presented. Irradiation of 2′,3′-0-isopropylidene-5′-deoxy-5′-phenylthioadenosine with 60W Hg vapor lamp afforded 2′,3′-0-isopropylidene-5′-deoxy-8,5′-cycloadenosine in high yield. The use of other 5′-alkylthio derivatives also gave the cycloadenosine, though the yields were rather poor. Deacetonation of the cyclo compound with 0.1N HC1 gave 5′-deoxy-8,5′-cycloadenosine. The cycloinosine derivative was similarly prepared. The nmr, mass and CD spectra of 5′-deoxy- 8,5′-cycloadenosine were given and discussed with the previously reported results.