Ring opening of a 4,9-dioxa-2-azabicyclo[4.2.1]nonane-3-thione

Abstract

S-Methyl N-(5-deoxy-5-iodo-2,3-O-isopropylidene-β-D-ribofuranosyl)N-(2-methoxycarbonylethyl)thiocarba-mate (IV) was formed by the action of methyl iodide on methyl 3-(7,8-isopropylidenedioxy-3-thioxo-4,9-dioxa-2-azabicyclo[4.2.1]nonan-2-yl)propionate (I), and a mixture of the corresponding N-(5-chloro-β-D-ribofuranosyl)-carbamoyl chloride (V) and bis-[N-(5-chloro-β-D-ribofuranosyi)carbamoyl] disulphide (VI) by treatment of compound (I) with thionyl chloride. Some reactions of the carbamoyl derivatives (V) and (VI) are described.