Palladium(0)-catalysed synthesis of 2, 3- and 3, 4-unsaturated aryl β-O-glycosides. (19th November 2015)

• Record Type: Journal Article
• Authors: Kubiak, Agnieszka; Kołodziuk, Robert; Porwański, Stanisław; Zawisza, Anna
• Is Part Of: Carbohydrate research. Volume 417(2015)
• Page Start: 34
• Page End: 40
• Publication Date: 2015-11-19
• Subjects: d-Glucal -- O-Glycosides -- Ferrier rearrangement -- Allylic alkylation reaction -- Homogeneous catalysis -- Palladium; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2015.08.016
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: Synthesis of new unsaturated carbohydrate. Palladium(0)-catalysed arylation of derivatived -glucal with various phenols. Synthesis of 2, 3- and 3, 4-unsaturated aryl β- O -glycosides. Structural characterisation was performed. Graphical abstract: 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.