A Concise Synthesis of Sugar Isoxazole Conjugates

Tetrahedron Letters 2013
Jevgeņija Lugiņina, Vitālijs Rjabovs, Sergejs Beļakovs, Māris Turks

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.

Atslēgas vārdi
Carbohydrates; Isoxazoles; Azoles; Glycoconjugates; Nitrile oxide; Dipolar cycloaddition
DOI
10.1016/j.tetlet.2013.07.103
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0040403913012628#

Lugiņina, J., Rjabovs, V., Beļakovs, S., Turks, M. A Concise Synthesis of Sugar Isoxazole Conjugates. Tetrahedron Letters, 2013, Vol.54, Iss.39, 5328.-5331.lpp. ISSN 0040-4039. Pieejams: doi:10.1016/j.tetlet.2013.07.103

Publikācijas valoda
English (en)