Methanol → HCID 14859953, compound

Participants

Reaction Steps

A mixture of 5'-O-trityladenosine (497 mg, 1 mmol) and dibutyltin oxide (249 mg, 1 mmol) in methanol (50 mL) is heated under reflux until a clear solution is obtained. The solution is concentrated in vacuo, the residue dissolved in dimethylformamide (20 mL). To the ice cooled solution is added triflyl chloride (190 mg, 1.1 mmol), and the mixture stirred for 90 minutes at room temperature, and then concentrated in vacuo. The residue is dissolved in pyridine (20 mL), and the solution treated with acetic anhydride (1.5 mL). After being stirred for 3 hours at room temperature, the mixture is concentrated in vacuo. The residue is chromatographed on a silica gel using a mixture of chloroform and ethanol (33:1 v/v) as the eluent to give 3'-O-acetyl-2'-O-triflyl-5'-O-trityladenosine (208) mg, 31%) as a foam. 1H NMR (Me2SO-d6) δ 2.12 (3H, s, OAc), 3.36-3.49 (2H, m, H-5'5"), 4.36-4.40 (1H, m, H-4'), 5.90-5.95 (1h, m, H-3'), 6.45-6.54 (2H, m, H-1',2'), 7.20-7.57 (17H, m, Tr, NH2), 8.06, 8.35 (1H each, s, H-2, H-8). Analyses: Calculated for C32 H28F3N5O7S: C, 71.94, H, 5.45, N, 10.24. Found: C, 71.67, H, 5.50, N, 10.27.

Provenance & Evidence