Abstract

AbstractRacemic 1′,4′‐dimethyladenosine was prepared according to a stereoselective sequence from 2,5‐dimethyl furan and vinylene carbonate. This sequence is short and efficient (nine steps) and relies on the desymmetrization of a meso diol, followed by the glycosylation of the anomeric position. The latter reaction was thoroughly studied, as it is the key step of the sequence, and very particular reactivity of the 1′,4′‐dimethylated sugars was observed. Secondary reactions took place according to original mechanisms and delivered original byproducts.

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