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

Autor: Suthagar K; Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand. antony.fairbanks@canterbury.ac.nz., Polson MI, Fairbanks AJ
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2015 Jun 21; Vol. 13 (23), pp. 6573-9. Date of Electronic Publication: 2015 May 18.
DOI: 10.1039/c5ob00851d
Abstrakt: 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.
Databáze: MEDLINE