Acetic Acid → 5'-Deoxy-5'-dimethylsulfonio-8-methyladenosine bromide

Participants

Reaction Steps

Compound 20a (78 mg, 0.25 mmol) in a 2:1 mixture (4 mL) of formic and acetic acid was treated with a 2M solution of bromomethane in diethyl ether (5 mL) and stirred for 6 days in darkness at room temperature. Solvents were removed in vacuo and a solution of the residue in water (10 mL) was extracted with (3×10 mL) ether. The aqueous layer was concentrated to dryness. The resulting product was dissolved in MeOH (10 mL), filtered and treated with diethyl ether to precipitate out the salt. The salt was filtered, washed with ether, and dried in vacuo to give white solid: yield 79 mg (78%); MS m/z 326 (M)+; 1HNMR (D2O) δ 8.24 (s, 1H, H-2), 6.03 (d, 1H, H-1′, J1′,2′=5.4 Hz), 5.29 (t, 1H, H-2′, J2′,3′=5.7 Hz), 4.80 (t, 1H, H-3′, J3′,4′=4.8 Hz), 4.52-4.60 (m, 1H, H-4′), 4.11-4.20 (m, 1H, 5′-CH2), 3.81-3.90 (m, 1H, 5′-CH2), 2.92 and 2.89 (2s, 6H, S—(CH3)2), 2.67 (s, 3H, 8-CH3).

Provenance & Evidence