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

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 fur...

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Veröffentlicht in:Organic & biomolecular chemistry 2015-06, Vol.13 (23), p.6573-6579
Hauptverfasser: Suthagar, Kajitha, Polson, Matthew I J, Fairbanks, Antony J
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Sprache:eng
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00851d