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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)

Monday, July 06, 2020

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