A fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker as a safety-catch linker

Abstract

We report on the fluorous-assisted synthesis of oligosaccharides using a phenyl ether linker. The phenyl ether linker is stable under both acidic and basic conditions but can be cleaved under mildly acidic conditions after reduction to a vinyl ether. The utility of the method was demonstrated by the synthesis of a trisaccharide. A protected trisaccharide with a light-fluorous tag was directly prepared by one-pot glycosylation using three building blocks that contained a building block with a light-fluorous tag though a phenyl ether. A Birch reduction of the trisaccharide provided a fully deprotected trisaccharide with the fluorous tag attached through a vinyl ether, which was easily purified by solid-phase extraction. The tag was cleaved from the sugar portion by treatment with 3% TFA in MeOH.