Condensation reactions of acetyl derivatives of β-D-galactopyranosylamine with chlorosilanes

Author: Dimitri Lashkhi
Keywords: N-glycoside, glycosylamine, galactopyranosylamine, galactose, potential biological activity
Annotation:

In order to obtain a new substances with potential biological activity, we studied the silylation reactions of N-galactopyranosylamines. By acetylating N-β-(p-tolyl)-D-galactopyranosylamine (2) in the presence of acetic anhydride in a pyridine medium, we obtained N-β-(p-tolyl)-2,3,4,6-tetra-O-acetyl-D-galactopyranosylamine (3). Then we chlorosilylated the obtained compound by reacting it with trimethylchlorosilane and triphenylchlorosilane in the presence of zinc at room temperature, resulting in N-β-(p-tolyl)-N-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-galactopyranosylamine (4) and N-β-(p-tolyl)-N-triphenylsilyl-2,3,4,6-tetra-O-acetyl-D-galactopyranosylamine (4').