In an effort to provide additional methods to facilitate oligosaccharides assembly, the synthesis and exploration of novel leaving groups must occur. Heterocyclic anomeric leaving groups have proven to be effective in the glycosylation reaction. This project details the synthesis, and initial investigation of the nitrogen containing bicyclic carbohydrate leaving group, 4,2’pyridine-2-mercaptopyrimidine. The bicyclic compound was added to glucose, galactose, and mannose providing a range of glycosyl donors. These donors were subjected to activation using thiophilic promoters to determine their potential in the glycosylation reaction and to study their steroselective outcome. Examination of these potential glycosyl donors is ongoing and includes the exploration of additional activators.

Investigation of 4,2’pyridine-2-mercaptopyrimidine glycosides

255th National Meeting (2018)

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