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:	FILHO,JOÃO RUFINO FREITAS, FREITAS,JUCLEITON JOSÉ RUFINO DE, COTTIER,LOUIS, SINOU,DENIS, SRIVASTAVA,RAJENDRA MOHAN
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2015
Materias:	Configuration Crystallographic data baker's yeast
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004
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spelling	oai:scielo:S0717-970720150004000042016-02-23SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIESFILHO,JOÃO RUFINO FREITASFREITAS,JUCLEITON JOSÉ RUFINO DECOTTIER,LOUISSINOU,DENISSRIVASTAVA,RAJENDRA MOHAN Configuration Crystallographic data baker's yeast 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.60 n.4 20152015-12-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004en10.4067/S0717-97072015000400004
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Configuration Crystallographic data baker's yeast
spellingShingle	Configuration Crystallographic data baker's yeast FILHO,JOÃO RUFINO FREITAS FREITAS,JUCLEITON JOSÉ RUFINO DE COTTIER,LOUIS SINOU,DENIS SRIVASTAVA,RAJENDRA MOHAN SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
description	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.
author	FILHO,JOÃO RUFINO FREITAS FREITAS,JUCLEITON JOSÉ RUFINO DE COTTIER,LOUIS SINOU,DENIS SRIVASTAVA,RAJENDRA MOHAN
author_facet	FILHO,JOÃO RUFINO FREITAS FREITAS,JUCLEITON JOSÉ RUFINO DE COTTIER,LOUIS SINOU,DENIS SRIVASTAVA,RAJENDRA MOHAN
author_sort	FILHO,JOÃO RUFINO FREITAS
title	SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
title_short	SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
title_full	SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
title_fullStr	SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
title_full_unstemmed	SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES
title_sort	synthesis of 2,3-unsaturated o-glycosides from optically active alcohols via ferrier rearrangement: configurational studies
publisher	Sociedad Chilena de Química
publishDate	2015
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072015000400004
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SYNTHESIS OF 2,3-UNSATURATED O-GLYCOSIDES FROM OPTICALLY ACTIVE ALCOHOLS VIA FERRIER REARRANGEMENT: CONFIGURATIONAL STUDIES

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