Predictable coupling of carbohydrates to form longer sugar chains is of great interest to glycoscientists. Therefore the selection of the anomeric leaving group moiety can prove to be quite import as its involvement during the glycosylation reaction is significant. Nitrogen containing heterocyclic leaving groups have been employed in the coupling reaction. Since hydrogen bonding can with the glycosyl donor containing a nitrogen atom and the glycosyl acceptor, there should be an influence on the stereooutcome of the coupled product. This is the investigation of interactions between the glycosyl donor and a glycosyl acceptor via hydrogen bonding. The number of nitrogens contained within the leaving group also has an impact on selectivity. Conditions such as solvent dilution and electrophilic promoter were employed in an effort determine the extent of the influence hydrogen bonding had on the final coupled product.

Hydrogen bonding of leaving group correlation to stereoselective outcome

255th National Meeting (2018)

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