Tetrahedron

3, 4-Dipyranosyl-1, 2, 5-oxadiazole 2-oxides: synthesis and X-ray structure

…, AR March, S Parsons, RM Paton, GW Stewart

Index: Baker, Kenneth W.J; March, Andrew R; Parsons, Simon; Paton, R.Michael; Stewart, Gavin W Tetrahedron, 2002 , vol. 58, # 42 p. 8505 - 8513

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Citation Number: 22

Abstract

3, 4-Di (2, 3, 4, 6-tetra-O-acetyl-β-d-mannopyranosyl)-1, 2, 5-oxadiazole 2-oxide (7) has been synthesised from d-mannose by a route involving as the key step dimerisation of mannopyranosyl nitrile oxide 2. Three methods were used for the generation of the nitrile oxide: isocyanate-mediated dehydration of nitromethylmannose derivative 4, treatment of aldoxime 5 with aq. hypochlorite, and base-induced dehydrochlorination of hydroximoyl ...