Synthesis of 3-methylpseudouridine and 2′-deoxy-3-methyl-pseudouridine

Akira Matsuda, Krzysztof W Pankiewicz, Bonita K. Marcus, Kyoichi A. Watanabe, Jack J. Fox

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The first chemical synthesis of 3-methyl-ψ-uridine (5) and its 2′-deoxy analogue (9) has been achieved. ψ-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 5 in 82% overall yield. Treatment of 5 with 1,3-dichloro-1,1,3,3-tetraiso-propyldisiloxane afforded the 3′,5′-protected product, which was converted into the 2′-O-[(imidazol-1-yl)thiocarbonyl] derivative 7. Reduction of 7 with tributyltin hydride followed by deblocking of the product gave crystalline 2′-deoxy-3-methyl-ψ-uridine (9) in 35% yield from 5.

Original languageEnglish (US)
Pages (from-to)297-302
Number of pages6
JournalCarbohydrate Research
Volume100
Issue number1
DOIs
StatePublished - 1982

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