title: Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity.
abstract: The synthesis of the title compounds using intramolecular nucleophilic substitution reactions in the molecules of the corresponding 2-alkoxycarbonylamino-2-deoxy glucosyl halides was studied. It was found that in contrast to the 2-alkyl (aryl) glyco-[2,1-d]-2-oxazolines, the synthesis of the target 2-alkoxy glyco-[2,1-d]-2-oxazolines was possible only in highly basic media. The synthesized 2-alkoxy oxazoline derivatives turned out to be active glycosyl donors and were used for stereoselective 1,2-trans glycosylation reactions catalyzed by weak protic acid under very mild conditions, thus preventing anomerization and other side reactions. As a result of this glycosylation, the glycoside and oligosaccharide derivatives containing urethane N-protecting groups were formed.
authors.affiliation: Department of Organic and Biological Chemistry, V.I. Vernadsky Taurida National University, Vernadsky ave. 4, 95007 Simferopol, Crimea, Ukraine. orgchem@crimea.edu
authors.forename: Sergey S
authors.initials: SS
authors.lastname: Pertel
authors.forename: Leonid O
authors.initials: LO
authors.lastname: Kononov
authors.forename: Alexander I
authors.initials: AI
authors.lastname: Zinin
authors.forename: Vasily Ja
authors.initials: VJ
authors.lastname: Chirva
authors.forename: Elena S
authors.initials: ES
authors.lastname: Kakayan
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D009844:Oligosaccharides; D010080:Oxazoles