5′-substituted-5′-deoxy nucleosides |
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Authors: | J.J. Baker A.M. Mian J.R. Tittensor |
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Affiliation: | Imperial Chemical Industries Ltd., Pharmaceuticals Division, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG U.K. |
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Abstract: | The methyl esters of the uronic acids derived from uridine, 5-fluorodeoxyuridine, 6-aza-2′-deoxyuridine and 2′,3′-o-isopropylideneadenosine were converted to the amides with aqueous d0·88 ammonia. After protection of the sugar hydroxyls each 5′-carboxamide was dehydrated with phosphoryl chloride at ?5° to yield, after deprotection, the respective novel 5′-nitrile nucleosides. Treatment of the protected 5′-nitrile nucleosides with ammonium azide in DMF gave, after deprotection, the novel 5′-C-tetrazole nucleosides. |
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