Reductions of Monosaccharide Derivative Epoxyamides to Epoxyalcohols and Regioselective Epoxide Opening

M. Pino-González; Noé Bernal; Antonio Romero

doi:10.3390/ecsoc-12-01226

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Reductions of Monosaccharide Derivative Epoxyamides to Epoxyalcohols and Regioselective Epoxide Opening

M. Soledad Pino-González

^*,

Noé Oña Bernal

Antonio Romero

¹ Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias.Universidad de Málaga. 29071 Málaga. Spain

Published: 10 November 2008 by MDPI in The 12th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-12-01226

Abstract: Amide group reduction in monosaccharide derivative 2,3-epoxyamides were accomplished with a combination of two reagents: RedAl and NaBH4, successively added at 0ºC, without affecting the epoxide group. The obtained epoxyalcohols could be regioselectively opened at the vicinal carbon to the hydroxymethyl group, by NaN3/Me3B without detection of another azido isomer.

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M. Pino-González

Noé Bernal

Antonio Romero