Abstract
The synthese of 1,3,7-trideaza-2',3'-dideoxyadenosine and its 2',3'-didehydroderivative as potential anti-HIV compounds are described. Nucleobase anion glycosylation of 4-nitroindole (4) with 1-dichloro-2-deoxy-3,(-bis-O-(4-methylbenzoyl)-α-D-erythro-pentofuranose yields 1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-4-nitro-1H-indole stereoselectively. Upon detoluoylation the 3'-hydroxyl group was removed by two different routes using a mesylation/elimination process
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