Highly Efficient Inversion of the C-3 Configuration in 1,2-O-Isopropylidenefuranose Derivatives by an Adapted Swern Oxidation/Sodium Borohydride Reduction Protocol in One Pot
DOI:
https://doi.org/10.29356/jmcs.v49i1.1316Keywords:
Inversion of the configuration, swern oxidation-sodium, borohydride reduction in one potAbstract
Abstract. One pot Swern oxidation-sodium borohydride reduction of
1,2-O-isopropylidenefuranose derivatives having the D-gluco or Dxylo
configurations led to the corresponding stereoisomers resulting from the stereoselective inversion of C-3. This method is a simple adaptation to the traditional procedure that consists in quenching the Swern oxidation at -60 ºC with a mixture of H2O/EtOH (1:4), in which NaBH4 is dissolved. Thus, the inversion of the configuration at C-3 of 1,2-O-isopropylidenefuranose derivatives is accomplished in yields up to 98%.
Resumen. La reacción de oxidación de Swern-reducción con borohidruro de sodio en un solo paso de los derivados de 1,2-O-isopropilidenofuranosa con configuración D-gluco o D-xilo, producen sus estereoisómeros correspondientes, los cuales provienen de la inversión estereoselectiva del C-3. Este método es una adaptación al procedimiento tradicional de oxidación de Swern, en donde al término de la reacción se adiciona una mezcla de H2O/EtOH (1:4) a -60 ºC, en la
cual se disuelve NaBH4. Así, la inversión de la configuración del C-3
en los derivados de 1,2-O-isopropylidenofuranosa se logra en rendimientos hasta del 98%.
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