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Publikācija: A Concise Synthesis of Sugar Isoxazole Conjugates

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language A Concise Synthesis of Sugar Isoxazole Conjugates
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Jevgeņija Lugiņina
Vitālijs Rjabovs
Sergejs Beļakovs
Māris Turks
Keywords Carbohydrates; Isoxazoles; Azoles; Glycoconjugates; Nitrile oxide; Dipolar cycloaddition
Abstract A synthesis of novel 3,5-disubstituted isoxazole–carbohydrate conjugates is described. The title compounds are obtained from 3-deoxy-3-C-nitromethyl derivatives of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose via nitrile oxide intermediates. The developed approach provides the first examples of isoxazolyl sugars where the azole fragment is attached to C(3) of the carbohydrate through a C–C bond. Isoxazoles can be valuable linkers in glycoconjugate chemistry and this is demonstrated by the synthesis of a glycocluster containing five carbohydrate residues attached to a central glucose platform.
DOI: 10.1016/j.tetlet.2013.07.103
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0040403913012628# 
Reference Lugiņina, J., Rjabovs, V., Beļakovs, S., Turks, M. A Concise Synthesis of Sugar Isoxazole Conjugates. Tetrahedron Letters, 2013, Vol.54, Iss.39, pp.5328-5331. ISSN 0040-4039. Available from: doi:10.1016/j.tetlet.2013.07.103
Additional information Citation count:
ID 16469