Synthesis of 5-deoxy-5-hydroxyphosphinyl-d-mannopyranoses

Tadashi Hanaya, Kunihiro Hirose, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    8 Citations (Scopus)

    Abstract

    The title sugar analogues (13) were synthesized by starting with known methyl (E)-5,6-dideoxy-2,3-O-isopropylidene-6-nitro-α-d-lyxo-hex-5-enofuranoside (5a) in six steps through the key intermediate, methyl 5-deoxy-5-dimethoxy-phosphinyl-2,3-O-isopropylidene-α-d-mannofuranoside 8a). The products (13) were converted into the corresponding penta-O-acetyl-5-methoxyphosphinyl derivatives (14), whose structures and conformations (mostly 4C1) were established by spectroscopy.

    Original languageEnglish
    Pages (from-to)2557-2564
    Number of pages8
    JournalHeterocycles
    Volume36
    Issue number11
    DOIs
    Publication statusPublished - Nov 1 1993

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

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