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Preparation of 2-acetamido-2-deoxy-β-D-glucopyranosyl-methylamine via nitromethane route

M. Petrušová, M. Fedoroňko, and L. Petruš

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-842 38 Bratislava

 

Abstract: Epimeric 3-acetamido-l,3-dideoxy-l-nitroheptitols formed in the ni­tromethane synthesis with N-acetyl-D-glucosamine were converted to 2-acetamido-2-deoxy-β-D-glucopyranosylnitromethane by intramolecular cyclodehydraiion. The compound was isolated as a salt of a strongly basic anion-exchange resin in the OH form, from which it was liberated by carbon dioxide. Reduction of the nitro derivative with iron(II) hydroxide in situ afforded 2-acetamido-2-deoxy-β-D-glucopyranosylmethylamine. Its struc­ture was proved by the , 13C NMR spectrometry.

Full paper in Portable Document Format: 442a267.pdf

 

Chemical Papers 44 (2) 267–271 (1990)

Monday, May 25, 2020

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