Condensation reaction of N-β-(para-tolyl)-2,3,4,6-tetra-O-acetyl-glucopyranosylamine with trimethylchlorosilane

Author: mariam chibukhashvili
Keywords: Carbohydrates, N glycosides, silicon atoms, chlorosilylation, acetylation
Annotation:

In order to obtain biological active compounds, we have devised a new metod for synthesizing silicon containing N-glycosides. Modification of known medicinal preparations with silicon atoms can result significant changes in chemical character and biological properties. We have studied the reaction of chlorosilylation of N-glucopyranosylamine. N-β-(p-tolyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranosilamine (2) was obtained by acetylation of N-β-(p-tolyl)-D-glucopyranosylamine (1) with acetic anhydride and pyridine. By chlorosilylation of compound (2) with trimethylchlorosilane and triphenylchlorosilane in the presence of zinc dustat at room temperature corresponding N-β-(p-tolyl)-N-trimethylsilyl-2,3,4,6-tetra-O-acetyl-D-glucopyranosilamines were synthesized for the first time. The reactions is carried out according to the following schem: The structures of obtained compounds were established by physical-chemical methods of analysis (IR and 13C-NMR, 1H-NMR spectroscopy).

Lecture files:

Condensation reactions of N-β(para-tolyl)2,3,4,6-tetra-O-acetyl-glucopyranosylamine with trimethylchlorosilane [en]
N-β-(პარა-ტოლილ)-2,3,4,6-ტეტრა-O-აცეტილ-გლუკოპირანოზილამინის კონდენსაციის რეაქცია ტრიმეთილქლორსილანთან [ka]