Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamatesElectronic supplementary information (ESI) available: Full experimental details for the synthesis and characterisation of all compounds, including associated spectra and X-ray crystal data of complexes (CIF), together with HPLC investigations into furanose/pyranose equilibration. CCDC 1029228, 1058601 and 1029227. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5o

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 fu...

Full description

Saved in:
Bibliographic Details
Main Authors: Suthagar, Kajitha, Polson, Matthew I. J, Fairbanks, Antony J
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Arabino N -glycosyl sulfamides, sulfonamides and sulfamates convert from the furanose to the thermodynamically preferred pyranose form in aqueous solution.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00851d