Magnus Björsne

Synthesis of 4-C-hydroxymethyl hexopyranosyl nucleosides as potential inhibitors of HIV

Abstract The synthesis of 1-(2,3,4-trideoxy-4-C-hydroxymethyl-β-D-erythro-hexopyranosyl)thymine ( 13 ); -uracil ( 15 ), -cytosine ( 16 ) and 9-(2,3,4-trideoxy-4-C-hydroxymethyl-β-D-erythro-hexopyranosyl)adenine ( 18 ) are described. The nucleoside analogues were evaluated for their anti-HIV activity in vitro.

Synthesis of mimics to thymidine triphosphate and 3'−deoxy−3'−fluorothymidine triphosphate

Abstract Nucleoside triphosphate isosteres 5′-deoxy-5′-[[[[(4-methylphenyl)sulfonyl] amino] carbonyl] amino] thymidine (1), 5′-deoxy-5′-[[[[(4-chlorophenyl) sulfonyl] amino] carbonyl] amino] thymidine (2), 5-[[[[(3-methyl-benzyl) sulfonyl] amino] carbonyl] amino] thymidine (7), 3′,5′-dideoxy-3′-fluoro-5′-[[[[(4-methylphenyl) sulfonyl] amino] carbonyl] amino] thymidine (9) and 3′-deoxy-3′-fluoro-5′-O-[[[(4-methylphenyl) sulfonyl] amino] carbonyl] thymidine (10) have been synthesized from 5′-deoxy-5′-aminothymidine and 3′-deoxy-3′-fluorothymidine.

Synthesis of 2′,3′-dideoxy-3′,4′-dihydroxymethyl substituted pyrimidine nucleoside analogues

Abstract Some 2′,3′-dideoxy-3′,4′-dihydroxymethyl nucleoside analogues have been synthesised using an aldol condensation followed by in situ cross Canizzaro reduction in order to introduce the 4′-hydroxymethyl group. Glycosylation using silylated pyrimidine bases furnished the 2′,3′-dideoxy-3′,4′-dihydroxymethyl nucleoside analogues.

Synthesis and Anti-viral Properties of 2′,3′-Dideoxy-3′,4′-dihydroxymethyl Substituted Pyrimidine Nucleoside Analogues

Abstract Some 2′,3′-dideoxy-3′, 4′-dihydroxymethyl nucleoside analogues have been synthesised starting from diacetone-D-glucose. The 3-C-hydroxymethyl group was introduced by selective hydroboration-oxidation of the 3-C-methylene derivative. The 4-C-hydroxymethyl group was obtained by an aldol condensation followed by in situ cross Canizzaro reduction. Glycosylation using silylated pyrimidine bases furnished the 2′,3′-dideoxy-3′,4′-dihydroxymethyl nucleoside analogues.