First synthesis of tepidopterin [2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-threo-biopterin]

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    8 Citations (Scopus)

    Abstract

    N2-(N,N-Dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-l-threo-biopterin (14) was prepared from l-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 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.

    Original languageEnglish
    Pages (from-to)2159-2162
    Number of pages4
    JournalCarbohydrate Research
    Volume342
    Issue number15
    DOIs
    Publication statusPublished - Nov 5 2007

    Keywords

    • Glycosylation
    • Pteridine
    • Pterin glycoside
    • Tepidopterin
    • l-threo-Biopterin

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Biochemistry
    • Organic Chemistry

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