Efficient total syntheses of natural pterin glycosides: limipterin and tepidopterin

Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    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
    JournalTetrahedron
    Volume64
    Issue number9
    DOIs
    Publication statusPublished - Feb 25 2008

    Keywords

    • Glycosylation
    • Protecting group
    • Pteridine
    • Pterin glycoside

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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