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Studies of Nucleosides and Nucleotides. XXV. Purine Cyclonucleosides. 2. Synthesis of 5'-Deoxyguanosine via an 5', 8-Cyclonucleoside
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1965
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BiosynthesisBioorganic ChemistryMesyl GroupBiochemistryEngineeringNatural SciencesNucleic Acid ChemistryPurine Cyclonucleosides5'-Di-o-mesyl DerivativeOligonucleotideDioxane-bromine BrominationStereoselective SynthesisPharmacologyEnzymatic ModificationPharmaceutical ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
8-Bromoguanosine was directly obtained from guanosine by means of dioxane-bromine bromination. Mesylation of 8-bromoguanosine gave 2', 5'-di-O-mesyl derivative, which was converted to 2'-O-mesyl-8-mercapto-5', 8-anhydroguanosine by the treatment with thiourea. Desulfurization of 5', 8-cyclonucleoside and subsequent removal of mesyl group gave 5'-deoxyguanosine. Acid hydrolysis of 2'-O-mesyl-5'-deoxyguanosine gave 2'-O-mesyl-5'-deoxyribose.