SYNTHESIS OF SOME NEW 3-NITROHEXOPYRANOSYLADENINES AND RELATED-COMPOUNDS VIA A NITROOLEFIN INTERMEDIATE AS POTENTIAL THERAPEUTIC AGENTS

Synthesis of a series of -benzylidene-3-nitro-beta-D-hexopyranosyl)ade nines (5, 6 and 7) was conducted. These were deprotected to the parent compounds 2, 3 and 4. The major glucopyranosyl isomer 6 with acetic a nhydride-pyridine gave o-2,3-dideoxy-3-nitro-beta-D-hexapyranosyl)aden ine (9), which was treated with morpholine, piperidine, allylamine, pr opargylamine, methyl glycinate, methanethiol sodium salt and thiopheno l in the presence of KF to afford the corresponding tro-2-(substituted )-beta-D-glucopyranosy)ladenines (10a-10g). These were deprotected to the compounds 11a-11g. The olefin 9 with sodium borohydride gave the 2 -deoxy analogue 12, which was deprotected to 13. Compound 10g with tri butyltin hydride-AIBN yielded the 2,3-didehydro-2,3-dideoxy analogue 1 4.