C-Nucleoside studies. Part 8. Synthesis of 3-β-D- arabinofuranosylpyrazole from D-mannose

J. Grant Buchanan, M. Encarnacion Chacón-Fuertes, Richard H. Wightman

Research output: Contribution to journalArticle

Abstract

Treatment of 3(5)-(1,2:4,5-di-O-isopropylidene-D-manno-pentahydroxypentyl) pyrazole (6) with acetone and concentrated sulphuric acid caused isomerisation to 3(5)-(2,3:4,5-di-O-isopropylidene-D-manno-pentahydroxypentyl)pyrazole (10). Reaction with 1-fluoro-2,4-dinitrobenzene and triethylamine, and subsequent treatment with methanesulphonyl chloride afforded 1-(2,4-dinitrophenyl)-3-(1-O- methylsulphonyl-2,3:4,5-di-O-isopropylidene-D-manno-pentahydroxypentyl)pyrazole (14) in 71% overall yield. On treatment with dilute hydrochloric acid in dioxan, or, preferably, with boron trichloride in dichloromethane followed by methanolysis, (14) afforded 1-(2,4-dinitrophenyl)-3-(ß-D-arabinofuranosyl) pyrazole (16) in up to 58% yield. Treatment of dinitrophenyl derivative (16) with methanolic ammonia gave an 86% yield of 3(5)-ß-D- arabinofuranosylpyrazole (2).

Original languageEnglish
Pages (from-to)244-248
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1979

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