Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

Tadashi Hanaya, Ken Ichi Sugiyama, Heizan Kawamoto, Hiroshi Yamamoto

    Research output: Contribution to journalArticlepeer-review

    20 Citations (Scopus)

    Abstract

    The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

    Original languageEnglish
    Pages (from-to)1641-1650
    Number of pages10
    JournalCarbohydrate Research
    Volume338
    Issue number16
    DOIs
    Publication statusPublished - Jul 29 2003

    Keywords

    • Deoxygenation
    • Phospho sugar
    • α-Hydroxyphosphonate

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Biochemistry
    • Organic Chemistry

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