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

Glycosylamines. 5.* Preparation, Structure, Anomeric Configuration and Conformation of Some N-Acetylglycosylamines and N-Acetyldiglycosylamines

K. Linek, J. Alföldi, T. Stach, and V. Pätoprsty

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

Abstract: N-Acetylation of (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine or bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine afforded N-acetyl-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine; deacetylation of the latter gave N-acetyl-di-β-D-glucopyranosylamine. Similarly, N-acetylation of bis(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)amine led to N-acetyl-bis(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)amine and its deacetylation to di-β-L-rhamnopyranosylamine. The structure, anomeric configuration and conformation of the above-mentioned compounds and also of N-acetyl-β-D-xylopyranosylamine, N-acetyl-2,3,4-tri-O-acetyl-β-D-xylopyranosylamine, N-acetyl-β-D-ribopyranosylamine, and N-acetyl-2,3,4-tri-O-acetyl-β-D-ribopyranosylamine were determined by ¹H, ¹³C NMR, and mass spectrometric methods.

Full paper in Portable Document Format: 506a359.pdf

Chemical Papers 50 (6) 359–364 (1996)