Regioselective synthesis of O- and O-cyclopyrimidine nucleoside analogues |
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Authors: | Dolores Viñ a,Elí as Quezada,Eugenio Uriarte |
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Affiliation: | a Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain b Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, 37008 Salamanca, Spain |
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Abstract: | Regioselective synthesis of two new series of cyclonucleoside analogues from the 1,2-carbonucleoside of uracil 1a: O2,7′-cyclonucleosides (3a-c) and O6,7′-cyclonucleosides (4a-c), analogues of pyrimidine (cyclohexane derivatives) is reported. Synthesis of O2-cyclonucleoside analogues was performed by activation of the hydroxymethyl group of carbocyclic moiety and using the carbonyl group at position 2 of the heterocyclic base as a nucleophile. Synthesis of O6-cyclonucleoside analogues was achieved by nucleophilic attack of the 7′-hydroxyl group on the electron-deficient 6-position and subsequently dehydrohalogenation in basic conditions. |
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Keywords: | Regioselective synthesis Cyclization Carbocycles Nucleosides Dehydrohalogenation |
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