C-nucleoside studies - 15. Synthesis of 3-β-D-arabinofuranosylpyrazoles and the D-arabinofuranosyl analogue of formycin

J. G. Buchanan, D. Smith, R. H. Wightman

Research output: Contribution to journalArticle

Abstract

A synthesis of 7-amino-3-(ß-D-arabinofuranosyl)pyrazolo[4,3-d]pyrimidine (13), the D-arabino analogue of formycin (1), from D-mannose is described. 1-(2,4-Dinitrophenyl)-3-(penta-O-acetyl-D-manno-pentahydroxypentyl)pyrazolewas converted into the 4-nitro-derivative 18 in 90% yield using trifluoroacetyl nitrate. In four steps 18 was transformed into the 3-ß-D-arabinofuranosylpyrazole 12 which gave the N-nitro derivative 24 in two further stages. Cine-substitution of the N-nitro group in 24 by cyanide ion was followed by elaboration of the pyrimidine ring to give 13. All the reactions proceeded with complete regio and stereoselectivity.

Original languageEnglish
Pages (from-to)119-123
Number of pages5
JournalTetrahedron
Volume40
Issue number1
DOIs
Publication statusPublished - 1984

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