STEREOCHEMISCHE ASPEKTE IN ZUSAMMENHANG MIT DER SYNTHESE VON 2,6-ANHYDRO-1-DESOXY-1-NITROALDITOLEN

Article abstract of DOI:10.1016/0008-6215(87)80143-X

2,6-Anhydro-1-deoxy-1-nitroalditols were prepared in good yields by known procedures via addition of nitromethane to D-glucose, D-mannose, D-galactose, D-xylose, D-lyxose and L-arabinose, followed by a cyclization step in boiling water.In the case of D-ribose, a mixture of pyranoid and furanoid anhydroalditols was isolated by different methods in relatively poor yields, at variance with recent reports by other authors.Establishment of the stereochemical relations of the products from ¹H-n.m.r. spectra of their acetates gave further insight into the diasteroselectivity of the cyclization step.