Ethanethiol → CHEBI:40460

Participants

Reaction Steps

3′-O-Benzoyl-N6-butyryl-2′-O-methyl adenosine 5′-H-phosphonate 10 (55 mg, 0.088 mmol) was dried by evaporation of added dry pyridine (5 mL) and 30 min drying on a vacuum pump. To the compound was added pyridine (0.8 mL), triethylamine (5 eq, 0.44 mmol, 61 μL) and trimethyl silyl chloride (5 eq, 0.44 mmol, 55.7 μL). The reaction was stirred for 15 min at room temperature, whereupon a solution of I2/H2O in pyridine (1.1 eq 12, 24 mg, 50 μL H2O, 500 μL pyridine) was added. After an additional 5 min a sample was taken and analysed by 31P NMR which showed complete oxidation. A drop of ethanethiol was added to achieve a colorless solution, the solvent was removed under reduced pressure and the crude compound was dissolved in MeOH/NH3 (sat.). The mixture was left overnight at room temperature, whereupon the solvent was removed under reduced pressure and the solid was dissolved in water. The aqueous solution was washed with diethyl ether (2×). The water layer was then collected, concentrated under reduced pressure and purified by RP-HPLC using a triethyl ammonium acetate buffer pH 6.5. RT=14 min (0-20 min 12% B, B=50% CH3CN). Yield 37% of compound 11 as triethyl ammonium salt (18.4 mg). 31P NMR (D2O) δ-1.02, 13C NMR δ 7.3, 22.4, 45.7, 57.2, 63.0, 68.3, 70.7, 82.3, 84.1, 84.4, 118.2, 126.5, 140.2, 148.2, 151.8, 154.6, 180.4, 199.5, MS (ES-TOF) m/z calculated: 361.08. found: 361.10.

Provenance & Evidence