The study of the acid-catalyzed reaction between 2-methyl and 2-(2,2,2-trichloroethoxy) gluco-[2,1-d]-2-oxazolines. Synthesis of macrocyclic pseudo-tetrasaccharide derivative of d-glucosamine.
The formation of macrocyclic pseudo-tetrasaccharide derivative of d-glucosamine as a result of the acid-catalyzed reaction between 2-methyl- and 2-(2,2,2-trichloroethoxy)-substituted oxazoline derivatives of sugars was discovered. The structure of the obtained product was determined using NMR spectroscopy and mass spectrometry. An explanation of the obtained results based on the mechanism of the reaction of electrophilic polymerization of 2-substituted glyco-[2,1-d]-2-oxazolines and the principle of hard and soft acids and bases (HSAB) was proposed.
['Pertel|Sergey S|SS|', 'Zinin|Alexander I|AI|', 'Seryi|Sergey A|SA|', 'Kakayan|Elena S|ES|']
D002236:Carbohydrate Conformation D002384:Catalysis D005944:Glucosamine D047028:Macrocyclic Compounds D009844:Oligosaccharides D010080:Oxazoles D013451:Sulfonic Acids
d-Glucosamine Alternating electrophilic copolymerization HSAB principle Macrocyclic oligosaccharides Oligosaccharide synthesis Sugar oxazoline derivatives