Green Biphasic Synthesis, X-Ray Diffraction Structure and Conformational Analysis of O-Glycosylmethyl Isoxazoles: Potential Substrates of GLUT-1 Glucose Transporter

Abstract

An efficient synthesis of new 1-O-β-glycosylmethyl isoxazoles is described. The title compounds are obtained by cycloaddition of nitrile oxides generated in situ in 2-MeTHF/sodium hypochlorite solution. The developed approach provides the first use of this green methodology to prepare isoxazole derivatives. X-ray diffraction structure and conformational analysis in solution show that glycosyl isoxazoles possess the structural features required to be substrates of GLUT-1.