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

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.

Palabras clave: Click-chemistry , Cycloaddition , O-Glycosides

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Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)

Identificadores

URI: http://hdl.handle.net/11336/215161

URL: https://onlinelibrary.wiley.com/doi/10.1002/slct.202104379

DOI: http://dx.doi.org/10.1002/slct.202104379

Colecciones

Articulos(CCT - LA PLATA)
Articulos de CTRO.CIENTIFICO TECNOL.CONICET - LA PLATA

Articulos(IFLP)
Articulos de INST.DE FISICA LA PLATA

Citación

Le Pors, Macarena Soledad; Barri, Ivan Alejandro; Riafrecha, Leonardo Ezequiel; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; Green Biphasic Synthesis, X-Ray Diffraction Structure and Conformational Analysis of O-Glycosylmethyl Isoxazoles: Potential Substrates of GLUT-1 Glucose Transporter; John Wiley & Sons; ChemistrySelect; 7; 4; 1-2022; 1-5

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