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Paper | Regular issue | Vol 34, No. 2, 1992, pp.265-272
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5890
Synthesis of 2',3'-Dideoxy-D-erythro-hex-2'-enopyranosyl Nucleosides from 5-Aminouracils and 3,4,6-Tri-O-acetyl-D-glucal

Henrik Pedersen, Erik B. Pedersen,* and Carsten M. Nielsen

*Department of Chemistry, Odense University, DK-5230 Odense M, Denmark

Abstract

Condensation of silylated N,N-disubstituted aminouracils (4) and 3,4,6-tri-O-acetyl-D-glucal (3) in the presence of TMS triflate as catalyst gave anomeric mixtures of 2',3'-dideoxy-D-erythro-hex-2'-enopyranosylnucleosides (5) and (6). The pure β- and α-anomers were separated by chromatography and deprotected with a saturated solution of ammonia in methanol to give 1-(2',3'-dideoxy-β-D-erythro-hex-2-enopyranosyl)-5-aminouracils (7) and their corresponding α-anomers (8), respectively. The anomeric configurations of these nucleosides were assigned by nmr analysis of the dihydro derivatives 9 and 10 obtained by hydrogeneration of 7a and 8a, respectively. No significant activity against HIV-1 was found.