Methanol → Cordycepin

Participants

Reaction Steps

Br-AcO-AR, 307 mg (0.741 mmoles), and 0.18 ml of triethylamine were dissolved in 30 ml of methanol and 620 mg of 2% palladium carbon was added to the solution. While stirring the mixture at room temperature, hydrogen gas was passed in a flow rate of 40 ml/min. After the palladium carbon was filtered, the filtrate was washed with ethanol and the solvent was distilled off under reduced pressure. The residue was dissolved in 8 ml of methanol and 0.4 ml of 28% sodium methoxide (methanolic solution) was added to the solution. The mixture was stirred at room temperature for 30 minutes. The reaction solution was quantitatively determined by HPLC, where 77.8 mg (0.33 mmoles) of 2',3'-dideoxyadenosine and 32.4 mg (0.30 mmoles) of 3'-deoxyadenosine were produced in yields of 45% and 17%, respectively. 300 MHz nuclear magnetic resonance spectra of the purified and isolated 2',3'-dideoxyadenosine and 3'-deoxyadenosine supported the structures of the products.

Provenance & Evidence