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Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives

Opened Access Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives

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Autor: Franconetti García, Antonio
Borrachero Moya, Pastora
Gómez Guillén, Manuel
Cabrera Escribano, Francisca
Departamento: Universidad de Sevilla. Departamento de Química orgánica
Fecha: 2013
Publicado en: Synlett, 24 (2), 249-253.
Tipo de documento: Artículo
Resumen: The reaction of phenylhydrazine with a sugar dialdehyde in water, as a key step for the synthesis of the 3-amino-3-deoxy-d-glucose moiety contained in kanamycin, has been revisited. Structural studies (IR and NMR as well as a simple theoretical model based on energy-minimization calculations and MD calculations) reported herein support the observed stereo- and regioselectivity. Efforts to improve the reproducibility and viability of the process as part of a convenient approach towards fluorinated kanamycin are also now presented.
Cita: Franconetti García, A., Borrachero Moya, P., Gómez Guillén, M. y Cabrera Escribano, F. (2013). Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives. Synlett, 24 (2), 249-253.
Tamaño: 264.2Kb
Formato: PDF

URI: http://hdl.handle.net/11441/62904

DOI: 10.1055/s-0032-1317783

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