Synthesis of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring (Phosphoro Sugar)

Tadashi Hanaya, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    Synthetic studies are reviewed on sugar analogs containing a phosphorus atom in the hemiacetal ring, e.g., analogs of d-xylo, d-gluco, 6-deoxy-l-galacto. d-mannopyranoses, as well as d-ribo and 2-deoxy-d-ribofuranoses. These compounds were converted into the corresponding per-O-acetyl derivatives, whose structures and conformations were established by 1H-NMR spectral analyses and partly by X-ray crystallographic analyses. Stereoselectivity of the introduction of a phosphinyl group to various types of 6-O-tosyl-hex-5-uloses and 6-nitro-hex-5-enoses are also described.

    Original languageEnglish
    Pages (from-to)377-387
    Number of pages11
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume51
    Issue number5
    DOIs
    Publication statusPublished - 1993

    Keywords

    • Addition of phosphonate
    • C-P bond
    • Chemical modification of carbohydrate
    • Cyclic phosphorus compound
    • Phosphoro sugar

    ASJC Scopus subject areas

    • Organic Chemistry

    Fingerprint

    Dive into the research topics of 'Synthesis of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring (Phosphoro Sugar)'. Together they form a unique fingerprint.

    Cite this