It has been established that hydrogen bonding influences the coupling outcome of carbohydrates during the glycosylation reaction. Additionally, it is known that solvents can have an impact on the stereoselective outcome of carbohydrates as well. Both of these concepts have been investigated without the glycosyl donor’s leaving group in mind. Because the predictability of coupled sugars is of great interest to carbohydrate scientists, careful selection of reaction conditions is needed. Here we report the use of nitrogen containing heterocyclic anomeric leaving groups and their role in the glycosylation mechanism when subjected to a variety of solvents and concentrations. What was investigated was the correlation of steroselectivity as hydrogen bonding increases, or decreases, depending on the choice of solvent. Furthermore, several thiophilic promoters also examined in an effort determine their effect on the outcome of the coupled products.

Solvent influences in leaving group based hydrogen bonding coupling of carbohydrates

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.