Concise syntheses of d-desosamine, 2-thiopyrimidinyl desosamine donors, and methyl desosaminide analogues from d-glucose

A concise synthesis of d-desosamine has been accomplished in five steps and in 15% overall yield from methyl α-d-glucopyranoside. Desosamine was then transformed into two known 2-thiopyrimidinyl donors (Woodward and Tatsuta donors), each in two steps. Finally, analogues of methyl desosaminide at the C-3 position were prepared (3-pyrrolidino, 3-piperidino, 3-morpholino) from a common 2,3-anhydrosugar intermediate.

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