Methanol → 2',3'-Didehydro-3'-deoxy-4'-ethynylthymidine

Participants

Reaction Steps

(2R,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (35 mg) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, potassium carbonate (72 mg) and methanol (3.5 mL) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was mixed with water and acetonitrile so as to form a uniform solution, and the solution was quantitated (LC). The yielded compound was found to be 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine (yield: 94%, calculated through quantitation) (internal standard: methyl phthalate). The 1H-NMR data of the compound are as follows.

Provenance & Evidence