We possess a never-ending desire to mimic nature’s elegances. This design principle has become a major aspiration in both art and science. For organic chemist this can be seen in the pursuit of the synthesis of natural products, as well as, in the design of new reaction catalysts that mimic enzyme efficiencies. Of all the aspects of enzyme catalyzed reactions to mimic of the selectivity of the glycosyltransferase stands as the “Holy Grail” in terms of substrate-, regio- and stereo-selectivity. Recently we have found that the use of the Taylor catalyst (Ph2BO(CH2)2NH2) as the regioselective activator component in a Pd(0)-catalyzed glycosylation (i.e., pyranone installation) can result in a reaction with glycosyl-transferase like selectivities. A reaction where this dual B/Pd-catalyst system mimics the nucleophilic and electrophilic activation sites of the enzyme. Key to this mimicry is the recognition that pyranone rings can serve as atomlessly protected forms of monosaccharides. In this regard, we have been working to develop practical catalytic asymmetric approaches to the synthesis and study of stereochemically complex oligosaccharide structural motifs, using of asymmetric catalysis. This reliance on catalysis for stereocontrol can be seen in the asymmetric synthesis of the key pyranone building blocks from achiral furans, the diastereoselective assembly of these pyranones in to oligomers and finally the regio- and stereoselective bidirectional-functionalization of these oligomers in to oligosaccharides. This effort and its application for oligosaccharide synthesis and related medicinal SAR-chemistry studies will be discussed.

De novo oligosaccharide synthesis and medicinal chemistry

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.