Resumen de Synthesis of 2,3-unsaturated o-glycosides from optically active alcohols via ferrier rearrangement: Configurational studies

João Rufino Freitas Filho, Jucleiton José Rufino de Freitas, Louis Cottier, Denis Sinou, Rajendra Mohan Srivastava

• 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.