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

Improved Method of Preparation of Glycosylmethylamines

B. Pribulová, M. Petrušová, V. Pätoprstý, and L. Petruš

Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava

E-mail: chemlpet@savba.sk

Received: 20 March 2003

Abstract: As shown especially for the transformation of the thermally rather unstable α -D-galactofuranosylnitromethane to α-D-galactofuranosylmethylamine, the electron-transfer reduction of glycosylnitromethanes with ferrous ions in aqueous ammonia at room temperature is a very mild and convenient alternative of the preparation of the corresponding glycosylmethylamines. Also β-L-rhamnopyranosylmethylamine, β-D-mannopyranosylmethylamine, β-D-galactopyranosylmethylamine, β-D-glucopyranosylmethylamine, and 2-acetamido-2-deoxy-β-D-glucopyranosylmethylamine were prepared by this improved method. Due to a simple isolation procedure the method gives 90—95 % yields of these interesting C-glycosyl compounds containing no isomeric products detectable by ¹H NMR spectroscopy. A preparation of β-L-rhamnopyranosylnitromethane is also described.

Full paper in Portable Document Format: 574a287.pdf

Chemical Papers 57 (4) 287–291 (2003)