Article
Toward fluorinated aminoglycosides: Structural studies of phenylhydrazine condensation with carbohydrate derivatives
Author/s | Franconetti García, Antonio
Borrachero Moya, Pastora Gómez Guillén, Manuel Cabrera Escribano, Francisca |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2013 |
Deposit Date | 2017-07-21 |
Published in |
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Abstract | 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 ... 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. |
Funding agencies | Agencia Española de Cooperación Internacional para el Desarrollo (AECID) Junta de Andalucía |
Project ID. | A/023577/09
A/030422/10 FQM 142 P09-AGR-4597 |
Citation | 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. |
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