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

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

Research output: Contribution to journalArticle

13 Citations (Scopus)

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. (C) 2009 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)6341-6347
Number of pages7
JournalTetrahedron
Volume65
Issue number32
DOIs
Publication statusPublished - 08 Aug 2009

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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