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 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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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. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c5ob00851d |