First synthesis of biopterin α-D-glucoside

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α- D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2'-O-(α-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N2-(N,N- dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl] biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.

    Original languageEnglish
    Pages (from-to)747-753
    Number of pages7
    JournalHeterocycles
    Volume77
    Issue number2
    DOIs
    Publication statusPublished - Feb 1 2009

    Keywords

    • Biopterine d-Glucoside
    • Protecting Group
    • Pteridine
    • Pterine Glycoside
    • Selective α-Glycosylation

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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