1,2-Cyclic sulfite and sulfate furanoside diesters: improved syntheses and stability

Christopher Hardacre, Ivano Messina, Marie E. Migaud, Kerry A. Ness, Sarah E. Norman

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The facile syntheses of 1,2- and 3,5-cyclic sulfite and sulfate furanoside diesters were conducted in molecular solvents and ionic liquids in the presence of immobilised morpholine. Molecular solvents and ionic liquids performed similarly with regards to overall yields. However, the use of ILs allowed for the reactions to be carried out under atmospheric conditions and showed good recyclability. Additionally, increases in product stability was achieved in ILs over organic solvents, in particular, in bis{(trifluoromethanesulfonyl)imide} and trispentafluoro-ethyltrifluorophosphate-based ionic liquids, which were also excellent media to control the hydrolysis of thionyl chloride and sulfuryl chloride.

    Original languageEnglish
    Pages (from-to)6341-6347
    Number of pages7
    JournalTetrahedron
    Volume65
    Issue number32
    DOIs
    Publication statusPublished - 8 Aug 2009

    Keywords

    • Carbohydrates
    • Cyclic-sulfate
    • Cyclic-sulfite
    • Ionic liquids

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