Synthèse de nucléosides pyrimidiques non protégés en O-2′ à partir de sulfites cycliques en C-1—C-2 |
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Authors: | Christian H Gagnieu Alain Guiller Henri Pacheco |
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Institution: | Institut National des Sciences Appliquées, Service de Chimie Biologique, Bât. 406, 20, av. A. Einstein, F-69621 Villeurbanne France |
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Abstract: | Treatment of 3,5,6-tri-O-benzoyl--
-glucofuranose 1,2-sulfite with an excess of bis(trimethylsil) uracil, in fusion processes without any catalyst, afforded an excellent yield of 1-(3,5,6-tri-O-benzoyl-2-O-trimethylsilyl-β-
-glucofuranosyl)uracil, which was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri-O-benzoyl-β-
-glucofuranosyl)uracil. This new synthetic method for nucleosides unprotected at O-2′ was also tested in other sugar series. In some cases, only the 1′,2′-trans-nucleosides were obtained, but in others, small yields (3–10%) of 1′,2′-cis-nucleosides were detected. The -to-β ratio seems to be dependent on the reaction temperature. 2,4-Dimethoxypyrimidine also reacted with sugar 1,2-sulfites and 4-O-methyl-1-(3,5,6-tri-O-benzyl-β-
-glucopyranosyl)-2-pyrimidinone was prepared in 85% yield from 3,5,6-tri-O-benzyl--
-glucopyranose 1,2-sulfite. |
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