SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES

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 unsaturated O-glycosides 7a-e. The crystallographic data of the glycosides 7b confirmed the (S)-configuration for the aglycone portion of the carbon atom.

Saved in:
Bibliographic Details
Main Authors: FILHO,JOÃO RUFINO FREITAS, FREITAS,JUCLEITON JOSÉ RUFINO DE, COTTIER,LOUIS, SINOU,DENIS, SRIVASTAVA,RAJENDRA MOHAN
Format: Digital revista
Language:English
Published: Sociedad Chilena de Química 2015
Online Access:http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004
Tags: Add Tag
No Tags, Be the first to tag this record!

Internet

http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004

Similar Items