ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Addition of 2,6-Anhydro-7-deoxy-7-nitro-L-glycero-L-galacto-heptitol to Formaldehyde and the Conversion of the Adduct to 3,7-Anhydro-D-glycero-L-manno-octulose

M. Petrušová, E. Lattová, M. Matulová, and L. Petruš

Institute of Chemistry, Slovak Academy of Sciences, CS-842 38 Bratislava

Abstract: The reaction of 2,6-anhydro-7-deoxy-7-nitro-L-glycero-L-galacto-heptitol with formaldehyde in dimethyl sulfoxide in the presence of sodium methoxide afforded a crystalline adduct which, by the ozonolysis in an aqueous solution at room temperature, was transformed to 3,7-anhydro-D-glycero-L-manno-octulose as a major product and 2,6-anhydro-D-glycero-L-manno-heptonic acid as a minor product. The products as well as the intermediates, 3,7-anhydro-2-deoxy-2-nitro-D-threo-L-galacto-octitol and its epimer 2,6-anhydro-7-deoxy-7-nitro-L-erythro-L-galacto-octitol, were characterized by the ¹H and ¹³C NMR spectrometry.

Full paper in Portable Document Format: 462a120.pdf

Chemical Papers 46 (2) 120–123 (1992)