Collect. Czech. Chem. Commun. 1993, 58, 902-908

The Use of Amberlite IRA-410 for Preparation of Terminal Chlorodeoxy Sugars

Nada Vukojevic, Dušan Miljković, Mirjana Popsavin and Velimir Popsavin

Institute of Chemistry, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Yugoslavia


Anion-exchange resin Amberlite IRA-410 was found to be an effective and selective reagent for the nucleophilic displacement of primary tosyloxy (mesyloxy) groups in 3,5-disulfonates of xylofuranose derivatives I and III, as well as in 3,5,6-trisulfontes and 3,6-ditosyl derivatives of glucofuranose V, VII and IX. In all examined cases only the primary sulfonyloxy groups were replaced with chloride anions, whereupon the corresponding terminal chlorodeoxy derivatives were obtained in good yields.