Sterically Congested 2,2-Dimethylphenylacetate Glycosyl Donors for Versatile Protecting-Group Manipulations and
Yan Tan1, Hui Xiao1, Menghan Li1
1State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai201203, China.
Abstract:
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.
Related Concept Videos
Protecting Groups for Aldehydes and Ketones: Introduction
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Protection of Alcohols
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Directing Effect of Substituents: ortho–para-Directing Groups
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry


