Silver-assisted gold-catalyzed solid phase synthesis of linear and branched oligosaccharides

Abstract

Unlike solid phase synthesis of peptides, synthesis of oligosaccharides by solid phase methods is lagging behind owing to inherent challenges faced while executing glycosidations. In this communication, silver-assisted gold-catalyzed glycosidations are found to be excellent for solid phase oligosaccharide synthesis. Glycosidations under catalytic conditions, one time coupling with four equivalents of donor, reactions in less than 30 min at 25 °C and on-resin deprotection of silyl and benzoate protecting groups are the salient features. Photocleaved glycans possess a protected amino functionality that can be utilized for bioconjugation. The versatility of this approach is established by synthesizing linear and branched pentaarabinofuranosides.