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

• Published in: Carbohydrate research Vol. 499; p. 108230
• Main Authors: Pertel, Sergey S., Zinin, Alexander I., Seryi, Sergey A., Kakayan, Elena S.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier Ltd 01-01-2021
• Subjects: Alternating electrophilic copolymerization; d-Glucosamine; HSAB principle; Macrocyclic oligosaccharides; Oligosaccharide synthesis; Sugar oxazoline derivatives; Sugar oxazoline derivatives; Alternating electrophilic copolymerization; Oligosaccharide synthesis; HSAB principle; Macrocyclic oligosaccharides; d-Glucosamine
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2020.108230

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.
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•Alternating copolymerization of 2-substituted glyco-[2,1-d]-2-oxazolines was revealed.•Cyclic tetrasaccharide forms by the reaction of 2-alkyl and 2-alkoxy glucooxazolines.•The HSAB concept provides an explanation for the formation of the alternating sequence of monosaccharide residues.