A synthesis of ψ-cytidine

Krzystof W. Pankiewicz, Kosaku Hirota, Akira Matsuda, Kyoichi A. Watanabe

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

A practical, seven-step synthesis of 5-(β-d-ribofuranosyl)cytosine (1, ψ-cytidine) was achieved. ψ-Uridine was converted into the 2′,3′-isopropylidene acetal 2 in 85% yield. Tosylation of 2 to the 5′-sulfonate 3, followed by deacetonation, afforded 5′-O-tosyl-ψ-uridine (6) in good yield. Treatment of 6 with 1,1′-carbonyldiimidazole afforded the 2′,3′-cyclic carbonate 10, which was converted into 4,5′-anhydro-2′,3′-O-carbonyl-ψ-uridine (11) by treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in N,N-dimethylformamide. 4,5′-Anhydro-ψ-uridine (7) was obtained in quantitative yield from 11 by decarbonylation in aqueous pyridine. Ammonolysis of 7 afforded ψ-cytidine (1) in good yield.

Original languageEnglish (US)
Pages (from-to)227-233
Number of pages7
JournalCarbohydrate Research
Volume127
Issue number2
DOIs
StatePublished - Apr 15 1984

Fingerprint Dive into the research topics of 'A synthesis of ψ-cytidine'. Together they form a unique fingerprint.

Cite this