STEREOSELECTIVE SYNTHESIS OF SOME 3-NITROGLUCOPYRANOSYLADENINE ANALOGS VIA A NITROOLEFIN INTERMEDIATE AS POTENTIAL THERAPEUTIC AGENTS

Three isomers of 9-(4,6-O-benzylidene-3-deoxy-beta-D-hexopyranosyl) ad enines (2-4) were isolated. The manno isomer 2 could be isomerized to the gluco isomer 3. The manno (2) and galacto isomer (4) were deprotec ted to 5 and 7, respectively. Michael addition of some organic amines and thiolates to the nitroolefin intermediate (8) gave the correspondi ng 2-(substituted)-3-nitro-glucopyranosides (9a-h). Compounds 9a,c,h w ere deprotected to l0a,c,h. Sodium azide with 8 gave the triazolo nucl eoside 11, which was deprotected to 12. 2-Deoxy-3-nitro analogue 14 wa s also obtained.