A highly stereoselective synthesis of 1-amino-2,5-anhydro-1-deoxyhexitols via 2-trifluoromethyl-oxazolinium intermediates

Jens Chr. Norrild, Christian Pedersen, Inger Søtofte

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    A series of 1-amino-2,5-anhydro-1-deoxyhexitols, namely derivatives of 1-amino-2,5-anhydro-1-deoxy-D-glucitol, -D-mannitol and D-talitol was prepared from the corresponding 1,3-dideoxy-1-trifluoroacetamido-D-ribo-hexitol and 1-deoxy-1-trifluoroacetamido-L-rhamnitol which both gave the expected C-2 inverted anhydrides. The reaction mechanism involves 2-trifluoromethyl-oxazolinium intermediates, which further undergo intramolecular attack of HO-5 at C-2 with inversion of the configuration. The reaction is stereospecific and highly regioselective. The crystal structure of 1-amino-2,5-anhydro-1-deoxy-D-glucitol hydrochloride is presented.
    Original languageEnglish
    JournalCarbohydrate Research
    Volume297
    Issue number3
    Pages (from-to)261-272
    ISSN0008-6215
    DOIs
    Publication statusPublished - 1997

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