Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin

Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)


    The key, versatile precursors N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from d-xylose (in 14 steps) and l-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.

    Original languageEnglish
    Pages (from-to)2090-2100
    Number of pages11
    Issue number9
    Publication statusPublished - Feb 25 2008


    • Glycosylation
    • Protecting group
    • Pteridine
    • Pterin glycoside

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry


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