New approach to synthesizing carbon-carbon bonds in carbohydrates

What is it about?

The formation of carbon-carbon bonds in carbohydrates provides important access to pharmacologically important therapeutics. We report that a Dess-Martin periodinane-mediated oxidative deprotection and olefenation of trimethylsilyl-protected carbohydrates can be used to form carbon-carbon bonds at C-6. We show that a variety of carbohydrates can be transformed using stabilized and non-stabilized yildes to generate the corresponding products in good to moderate yield. We also report on a quantitative deprotection of these protected carbohydrates using a resin-based acidic ethanolysis approach.

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Photo by Terry Vlisidis on Unsplash

Photo by Terry Vlisidis on Unsplash

Why is it important?

These alkenoates are important intermediates that can be used in carbohydrate synthesis diversity strategies to generate therapeutics with appropriate properties. Furthermore, our approach leaves the anomeric carbon unaffected, allowing for further functionalization at that carbon. This approach is scalable and greener than alternative approaches which use toxic chromium reagents.