Chemical synthesis study demonstrates robust DMPA glycosyl donors with high alcoholysis stability, indicating a streamlined approach for one-pot complex oligosaccharide assembly.
We report glycosyl 2,2-dimethyl-2′-(4-methoxyphenylethynyl)phenylacetates (DMPA) as a new class of glycosyl donors featuring exceptional stability toward alcoholysis and broad compatibility with protecting-group manipulations. The sterically congested DMPA donors can be readily prepared through coupling with the corresponding acid or via late-stage installation of a reactive alkyne handle, providing a versatile platform for the construction of latent-active glycosyl donors. These donors are efficiently activated under NIS/TMSOTf conditions but remain dormant under Au(I) catalysis; notably, treatment with TMSOTf alone affords only a trace amount of product, which enables orthogonal one-pot glycosylation strategies. The combination of synthetic robustness, broad substrate scope, and protecting-group-manipulation compatibility provides a practical approach for the streamlined synthesis of complex oligosaccharides and glycoconjugates.
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Tan et al. (2026) studied this question.
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