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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03152
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- Leverhulme Trust [RPG-2020-273]
An efficient two-step procedure for synthesizing pyrimidine nucleosides is described. Firstly, a series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared, followed by transacylation reaction to obtain uridine-5-carboxylic acid derivatives and related nucleosides.
An efficient two-step procedure for the syntheses of pyrimidine nucleosides is presented. A series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared from beta-anomeric isonitriles by reaction with Meldrum's acid or by allowing aminomethylene Meldrum's acid to react with an 1-aldofuranosyl halide or acetate. The resultant 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives underwent reaction with benzyl-or 2,4-dimethoxybenzyl isocyanate via transacylation to provide uridine-5-carboxylic acid derivatives and related nucleosides. These nucleoside carboxylic acids were converted into other C-5 derivatives by bromo-decarboxylation with N-bromosuccinimide.
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