"Synthesis and study of N-β-N-nitroso- (p-nitrophenyl) -2,3,4-tri-O-acetyl-L- arabinopyranosylamine."

Author: Ana Kikava
Keywords: L-arabinose, condensation, nitroso (-N=O) group.
Annotation:

Annotation Ana Kikava "Synthesis and study of N-β-N-nitroso- (p-nitrophenyl) -2,3,4-tri-O-acetyl-L- arabinopyranosylamine." Iv.Javakhishvili Tbilisi State University, Department of Chemistry I.Chavchavadze Ave. 3 In recent years, the synthesis of carbohydrates into various types of organic compounds has played an important role in the synthesis of new, biologically and pharmacologically active compounds. There is little information in the literature about carbohydrates contained in the nitrogen group. The use of glycosides to modify biologically active organic compounds can alter their biological and physiological action on the one hand and reduce their toxicity on the other. The goal of present investigation consist in synthesis of N-β-L-arabinopyranosylamines containing nitrosogroup. The starting material was the condensation product of L-arabinose (1) with p- nitroaniline - N-β- (p-nitrophenyl) - L-arabino-pyranosylamine (2). (2) Acetylation with acetic anhydride in the presence of sodium acetate in the pyridine region and nitrosation of the resulting compound - N-β - (p-nitrophenyl) -2,3,4-tri-O-acetyl-L-arabinopyranosylamine (3) With sodium nitrite (NaNO2), N-β-N-nitroso-(p-nitrophenyl)-2,3,4-tri-O-acetyl-L-arabinopyranosyl-amine (4) was synthesized. The reaction is carried out according to the following scheme: OH HO H HO H2N CH3OH NO2 H OH HO OH H,OH H1 HO OH H2 N NO2 (CH CO) O, OAc H 32O2 OAc HO OAc NaNO CH3COONa H CH2CI2 H AcO H Py; 00 AcO OAc p-TSA HNNO2 H N NO2 N=O 3H4 The structures of obtained compounds were established by physical-chemical methods of analysis. Key word: L-arabinose, condensation, nitroso (-N=O) group.