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

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

doi:10.1016/j.tet.2009.06.013

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 journal › Article › peer-review

18 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 language	English
Pages (from-to)	6341-6347
Number of pages	7
Journal	Tetrahedron
Volume	65
Issue number	32
DOIs	https://doi.org/10.1016/j.tet.2009.06.013
Publication status	Published - 08 Aug 2009

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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AU - Hardacre, Christopher

AU - Messina, Ivano

AU - Migaud, Marie

AU - Ness, K.A.

AU - Norman, Sarah

PY - 2009/8/8

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AB - 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.

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

Abstract

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