Improved Method of Preparation of Glycosylmethylamines

Pribulová, B., Petrušová, M., Pätoprstý, V. and Petruš, L. Improved Method of Preparation of Glycosylmethylamines Chemical Papers, Vol.57, No. 4, 2003, 287-291

Document type: Článok z časopisu / Journal Article
Collection: Chemical papers  
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Author(s) Pribulová, B.
Petrušová, M.
Pätoprstý, V.
Petruš, L.
Title Improved Method of Preparation of Glycosylmethylamines
Journal name Chemical Papers
Publication date 2003
Year available 2003
Volume number 57
Issue number 4
ISSN 0366-6352
Start page 287
End page 291
Place of publication Poland
Publisher Versita
Collection year 2003
Language english
Subject 290000 Engineering and Technology
290600 Chemical Engineering
Abstract/Summary 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.
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