Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides

Agnieszka Kubiak; Robert Kołodziuk; Stanisław Porwański; Anna Zawisza

doi:10.1016/j.carres.2015.08.016

Palladium(0)-catalysed synthesis of 2,3- and 3,4-unsaturated aryl β-O-glycosides

Carbohydr Res. 2015 Nov 19:417:34-40. doi: 10.1016/j.carres.2015.08.016. Epub 2015 Sep 5.

Authors

Agnieszka Kubiak¹, Robert Kołodziuk¹, Stanisław Porwański¹, Anna Zawisza²

Affiliations

¹ Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland.
² Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, 91-403 Łódź, Poland. Electronic address: azawisza@chemia.uni.lodz.pl.

PMID: 26406453
DOI: 10.1016/j.carres.2015.08.016

Abstract

Arylation of 6-O-tert-butyldiphenylsilyl-3,4-di-O-isobutyloxycarbonyl-d-glucal (3) with various phenols in the presence of a catalytic amount of palladium(0) gave the corresponding 2,3- and 3,4-unsaturated β-O-glycosides. The reaction is stereospecific, in all cases, only the β-anomer is formed.

Keywords: Allylic alkylation reaction; Ferrier rearrangement; Homogeneous catalysis; O-Glycosides; Palladium; d-Glucal.

MeSH terms

Alkylation
Catalysis
Deoxyglucose / analogs & derivatives*
Glycosides / chemical synthesis*
Molecular Structure
Palladium / chemistry*
Phenols / chemistry*
Stereoisomerism

Substances

Glycosides
Phenols
Palladium
Deoxyglucose