Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose

Tadashi Hanaya, Ken Ichi Sugiyama, Yasushi Fujii, Akihito Akamatsu, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)


    The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-α-L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by 1H-NMR spectroscopy.

    Original languageEnglish
    Pages (from-to)1301-1309
    Number of pages9
    Issue number7
    Publication statusPublished - Jul 1 2001


    • C-P bond
    • Deoxygenation
    • Heterosugar
    • Hexofuranos-5-ulose
    • Phosphorinane

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry


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