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Issue 23, 2015
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Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

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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.

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

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Publication details

The article was received on 28 Apr 2015, accepted on 12 May 2015 and first published on 12 May 2015


Article type: Paper
DOI: 10.1039/C5OB00851D
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 6573-6579
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    Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

    K. Suthagar, M. I. J. Polson and A. J. Fairbanks, Org. Biomol. Chem., 2015, 13, 6573
    DOI: 10.1039/C5OB00851D

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