N dlikozidebis qlorsilireba trimetil nqlorsuilanit da trifenilqlorsiulanit

Author: Mikheil Diakonidze
Co-authors: mikheil diakonidze
Annotation:

nnotation Mikheil Diakonidze The chlorosilylation of N- (p-Tolyl)-2,3,4,6-tetra-O-acetyl- β-Dglucopyranosylamine by triphenylchlorosilane and trimetilchlorosilane Iv. Javakhishvili Tbilisis State University, Departament of Chemistry I.Chavchavadze ave.3 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- and N-β-(p-tolyl)-N-triphenylsilyl-2,3,4, 6-tetra-Oacetyl-D-glucopyranosilamines (3 and 4) were synthesized for the first time. The reactions is carried out according to the following schem: O HO HO OH N CH3 O HO HO OH ~ OH NH2 COOC2H5 H C2H5OH + / 1 2 O AcO AcO OAc N CH3 H 3, 4 Ac2O H py O AcO AcO OAc N SiR3 CH3 ClSiR3 Zn - HCI R= CH3 (3); C6H5 (4) 0 0C OH OH OAc OAc The structures of obtained compounds were established by physical-chemical methods of analysis (IR and 13C-NMR, 1H-NMR

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