Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin

Tadashi Hanaya, Hiroki Baba, Hiroki Toyota, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    l-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.

    Original languageEnglish
    Pages (from-to)7989-7997
    Number of pages9
    JournalTetrahedron
    Volume65
    Issue number38
    DOIs
    Publication statusPublished - Sep 19 2009

    Keywords

    • Glycosylation
    • Protecting group
    • Pteridine
    • Pterin glycoside
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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