20204-84-6Relevant articles and documents
3,4-Dipyranosyl-1,2,5-oxadiazole 2-oxides: Synthesis and X-ray structure
Baker, Kenneth W.J,March, Andrew R,Parsons, Simon,Paton, R.Michael,Stewart, Gavin W
, p. 8505 - 8513 (2002)
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 chloride 6. D-Gluco, D-galacto, D-xylo, and L-fucopyranosyl analogues 8-11 were prepared similarly. The structure of D-mannose-derived 1,2,5-oxadiazole 2-oxide 7 was established by X-ray crystallography.