During the last decade, the Sharpless’s concept of click chemistry was transplanted to carbohydrate chemistry1-3. While, the original alkyne-azide reaction is well known, the alternative thiol-click is relatively unexplored. We were one of the first to expand the click chemistry to addition of thiols to enones [1]. Recent developments in thio-click chemistry [1,2] became a well-accepted part of the click reaction [4] toolbox. In our laboratory we have worked with some very interesting carbohydrate derived synthons belonging to enones 1-3 which offer a rigid conformation and can be easily hydrolyzed to hexoses in the pyranoside form. Since these chiral enones easily enter Michael additions they serve as ideal models for studying carbohydrate thio-click reactions and can be used in synthesizing a huge variety of diverse thiosugars and other compounds. Here are some examples: Another area I found the Sharpless’s concept exceptionally useful is when one needs to couple larger molecules but it is clear that they will be decoupled later on. Together with R. Bielski we proposed [3,4] to employ two different click reactions to couple both molecules to an entity we call sacrificial unit. The decoupling takes place via the destruction of this sacrificial functionality. The following scheme shows the strategy. 1. Z. J. Witczak, D. Lorchak, N. Nguyen, Carbohydr. Res., 342, 1929-1931, 2007 2.Z. J. Witczak, Phosphorus, Sulfur & Silicon and the related Elements, 188, 237-244, 2012 3. R. Bielski, Z. J. Witczak, Chem. Rev, 113, 2205-2243, 2013. 4. Click Chemistry in Glycoscience: New Development and Strategies, Edited by Z. J. Witczak, R. Bielski, John Wiley & Sons, New York, 2013.

Thio-click tools and coupling strategies for synthesis of carbohydrate glycomimetics

251st National Meeting (2016)

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