SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanones 4a-e have been reduced to optically active 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanols 5a-e with baker's yeast. We subjected the alcohols possessing (S)-configuration to Ferrier' rearrangement with tri-O-acetyl-D-glucal 6 which furnished new unsat...
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| Autores principales: | , , , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2015
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004 |
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| Sumario: | 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanones 4a-e have been reduced to optically active 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanols 5a-e with baker's yeast. We subjected the alcohols possessing (S)-configuration to Ferrier' rearrangement with tri-O-acetyl-D-glucal 6 which furnished new unsaturated O-glycosides 7a-e. The crystallographic data of the glycosides 7b confirmed the (S)-configuration for the aglycone portion of the carbon atom. |
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