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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 23(13), p. 6573-6579

DOI: 10.1039/c5ob00851d

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Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

Journal article published in 2015 by Kajitha Suthagar, Matthew I. J. Polson ORCID, Antony J. Fairbanks
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in the alkyl chain stopped mutarotation and furanose / pyranose equilibration, allowing the isolation of the first unprotected furanose N-glycosyl sulfonamide.