Abstract Cycloaddition of the azide derivative 5 with 1, 4-dihydroxybutyne afforded the N-thio- acyclic nucleoside 6, which prepared alternatively from coupling of the bromo derivative 8 with 2-acetoxy-ethylmercaptan. Deblocking of 6 gave the free nucleoside 7. Mesylation of 6 furnished the dimesylate 9, which gave three rearranged products 14–16 on treatment with chloride anion. These compounds might be obtained via the episulfonium ion 10, which is ...