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Synthesis 1991; 1991(11): 959-962
DOI: 10.1055/s-1991-26616
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Synthesis of 3-(1,2,4-Triazol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosyl and 3-(1,2,4-Triazol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosyl Uracils via an α,β-Unsaturated Aldehydohexose

Krzysztof Walczak* , Erik B. Pedersen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230, Odense M, Denmark
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Publication Date:
29 April 2002 (online)

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(4S,5R) (E)-4,6-Diacetoxy-5-hydroxy-2-hexenal (2) was synthesized from 3,4,6-tri-O-acetyl-D-glucal (1). 1,2,4-Triazole was coupled in a Michael-type addition reaction to 2 at C-3 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give after acetylation an isomeric mixture of 1,4,6-tri-O-acetyl-2,3-dideoxy-3-(1, 2,4-triazol-1-yl)-α-D-arabino-hexopyranoside (3 and 1,5,6-tri-O-acetyl-2,3-dideoxy-3-(1,2,4-triazol-1-yl)-α,β-D-ribo-hexofuranosides (4). Reaction of this mixture with silylated 2,4-dihydroxypyrimidines 5 in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst afforded nucleosides 6-8. The pure isomers, obtained by high-performance liquid chromatography, were deacetylated with 33% methylamine in absolute ethanol to give the corresponding nucleosides 9-11.