An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins

Tadashi Hanaya, Kazuyuki Soranaka, Koichiro Harada, Hiroshi Yamaguchi, Ryo Suzuki, Yusumi Endo, Hiroshi Yamamoto, Wolfgang Pfleiderer

    Research output: Contribution to journalArticlepeer-review

    4 Citations (Scopus)


    N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1′,2′-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2′-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).

    Original languageEnglish
    Pages (from-to)299-310
    Number of pages12
    Issue number1
    Publication statusPublished - Jan 1 2006

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry


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