Collect. Czech. Chem. Commun. 1998, 63, 1056-1059
https://doi.org/10.1135/cccc19981056

Facile Synthesis of 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone

Nada Vukojevica, Tatjana Dramicanina, Biljana Pericb, Mirjana Popsavinb, János Csanádib and Dušan Miljkovićb

a Department of Organic Chemistry, Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Yugoslavia
b Institute of Chemistry, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Yugoslavia

Abstract

A two-step synthesis of 1,2-anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone (1) has been achieved starting from D-glucofuranurono-6,3-lactone (2). Tosylation of 2 gave a mixture of 5-monotosylate 3 and 2,5-ditosylate 4 which were separated by crystallization followed by column chromatography. Acetylation of 3 gave 1,2-di-O-acetyl-5-O-tosyl-β-D-glucofuranurono-6,3-lactone (5) in the good yield. Treatment of ditosylate 4 with potassium carbonate in dry acetone afforded 1,2-anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone in 50% yield.

Keywords: D-Glucofuranurono-6,3-lactone; 1,2-Anhydro-5-O-tosyl-β-D-mannofuranurono-6,3-lactone; 1,2-Anhydrosugars; Carbohydrates; Uronolactones.