The para-methoxybenzyl (PMB) protecting group is widely used in carbohydrate synthesis because it is readily cleaved oxidatively in the presence of other protecting groups. However, the PMB group is unstable under many acidic glycosylation conditions. Herein, we report investigations using 3-methoxybenzyl for the protection of carbohydrate hydroxyls. The meta-methoxybenzyl protecting group proved to be stable under acidic glycosylation conditions. Methods to cleave the group as well as its applications in the automated solution-phase synthesis of oligosaccharides will also be discussed.

<i>Meta</i>-methoxybenzyl protecting groups for the protection of hydroxyls in carbohydrate synthesis

246th National Meeting (2013)

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Meta-methoxybenzyl protecting groups for the protection of hydroxyls in carbohydrate synthesis