Nucleosides. 131. the Synthesis of 5-(2-Chloro-2-Deoxy-3-D-Arabino-Furanosyduracil. Reinterpretation of Reaction of ψ-Uridine with A-Acetoxyisobutyryl Chloride. Studies Directed Toward the Synthesis of 21-Deoxy-21-Substituted Arabinq-Nucleosides. 2

Krzysztof W. Pankiewicz, Kyoichi A. Watanabe*e

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Abstract

Treatment of -uridine (3) with a-acetoxyisobutyryl chloride in acetonitrile gave, after deprotection, a mixture of four products: 5-(2-chloro-2-deoxy-B“D-arabinofuranosyljuracil (10a), its 3’-chloro xylo isomer (11a), 2l-chloro-2'-deoxy--uridine (9a) and 4,2’-anhydro--uridine (8a). Each component was isolated by column chromatography. Compound 9 was converted to the known 1,3-dimethyl derivative 2 by treatment with DMF-dimethylacetal. Treatment of 10 and 1_1 with NaOMe/MeOH afforded the same 4,2’-anhydro-C-nucleoside 8. The 1,3-dimethyl analogues of TO and 11, however, were converted to 2‘,3’-anhydro-l,3-dimethyl-i(j-uridine (13) upon base treatment. The epoxide 13 was also prepared in good yield by treatment of 10 and 11_ with DMF-dimethyl acetal.

Original languageEnglish (US)
Pages (from-to)613-624
Number of pages12
JournalNucleosides and Nucleotides
Volume4
Issue number5
DOIs
StatePublished - Dec 1 1985

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