A Second-Generation Tandem Ring-Closing Metathesis Cleavable Linker for Solid-Phase Oligosaccharide Synthesis

Abstract

A tandem ring-closing metathesis cleavable linker system for solid-phase oligosaccharide synthesis has been developed. The acid- and base-stable linker can be readily cleaved with Grubbs second-generation catalyst without the use of alkene additives to liberate the assembled oligosaccharides from the solid support. Application of the linker was shown in three solid-phase oligosaccharide synthesis campaigns. Two frame-shifted hyaluronic acid fragments were prepared, and we also report the synthesis of a trimeric β-1,3-glucan fragment, in which, next to the linker, our recently reported 4-azido-2,2-dimethylbutanoyl (AzDMB) protective group was applied.