A novel 4,5-dibromooctane-1,8-diol linker for solid-phase oligosaccharide synthesis

Abstract

A novel 4,5-dibromooctane-1,8-diol linker was applied to the solid support preparation of a β-(1→6) trisaccharide employing electrophilic activation of thioethyl glycoside building blocks. Debromination of the resin-bound linker-double bond could effectively be carried out by elimination, followed by olefin cross-metathesis revealing the desired trimeric n-pentenyl glycoside. High-resolution Magic Angle Spinning NMR spectroscopy was used as an analytical tool for the monitoring and development of the solid-phase reactions.