A new, lipophilic p-alkoxybenzyl ether protecting group and its use in the synthesis of a disaccharide

formula: see text] In contrast to major advances in the chemical synthesis of oligosaccharides, the methods of purification of the intermediates are essentially the same as they were decades ago. Here, the synthesis of p-(dodecyloxy)benzyl chloride is described and it is demonstrated that the new p-(dodecyloxy)benzyl ether protecting group can render a protected disaccharide sufficiently lipophilic for selective adsorption on C18 silica, thus sidestepping the expensive silica gel chromatography traditionally used for the isolation of protected oligosaccharides.