caa a22 4500 469038837 CHVBK 20180323132804.0 cr unu---uuuuu 170328e19920401xx s 000 0 eng 10.1007/BF00810947 doi (NATIONALLICENCE)springer-10.1007/BF00810947 Synthesis of 1-(3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy- L-arabino -hexofuranosyl)uracils via an α,β-unsaturated aldehydrohexose [Elektronische Daten] [Krzysztof Walczak, Jesper Wengel, Erik Pedersen] Synthese von 1-(3-(1,2,4-Triazol-1-yl)-2,3,6-trideoxy- L-arabino -hexofuranosyl)uracilen über eine α,β-ungesättigte Aldohexose Summary: Mercuric catalyzed hydrolysis of acetylatedL-rhamnal1 gave the α,β-unsaturated aldehyde2. 1,2,4-Triazole was coupled, in a Michael type addition reaction, to2 at C-3 in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to give, after acetylation at the anomeric center, an anomeric mixture of 1,5-di-O-acetyl-3-(1,2,4-triazol-1-yl)-2,3,6-trideoxy-L-arabino-hexofuranose (3). Reaction of3 with silylated 2,4-dihydroxypyrimidines4 in the presence of trimethylsilyl triflate as catalyst followed by deprotection with 33% methylamine in absolute ethanol afforded the corresponding nucleosides7 and8. Springer-Verlag, 1992 Michael type addition nationallicence L -Nucleosides nationallicence 2′,3′,6′-Trideoxy- L -hexofuranose nucleosides nationallicence 3′-(1,2,4-Triazol-1-yl) nucleosides nationallicence Walczak Krzysztof Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut Wengel Jesper Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut Pedersen Erik Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/4(1992-04-01), 349-354 0026-9247 123:4<349 1992 123 706 https://doi.org/10.1007/BF00810947 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00810947 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Walczak Krzysztof Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut NATIONALLICENCE 700 1- Wengel Jesper Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut NATIONALLICENCE 700 1- Pedersen Erik Department of Chemistry, Odense University, DK-5230, Odense M, Denmark aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/4(1992-04-01), 349-354 0026-9247 123:4<349 1992 123 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer