An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin

Tadashi Hanaya, Kiyoshi Torigoe, Kazuyuki Soranaka, Hiroshi Fujita, Hiroshi Yamamoto, Wolfgang Pfleiderer

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

    Original languageEnglish
    Pages (from-to)72-78
    Number of pages7
    JournalPteridines
    Volume19
    Issue number3
    DOIs
    Publication statusPublished - Sep 2008

    Keywords

    • Biopterin D-riboside
    • Glycosylation
    • Protecting groups
    • Pterin glycoside

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Medicine
    • Clinical Biochemistry

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