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

@article{Suthagar2015UnexpectedFE,
  title={Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates.},
  author={Kajitha Suthagar and Matthew I. J. Polson and Antony John Fairbanks},
  journal={Organic & biomolecular chemistry},
  year={2015},
  volume={13 23},
  pages={
          6573-9
        }
}
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. 

Topics from this paper.