Ethanol → HCID 16082777, compound

Participants

Reaction Steps

A mixture of 1-benzylinosine (3.58 g, 10 mmol) and trityl chloride (3.3 g, 12 mmol) in pyridine (50 mL is stirred overnight at room temperature. An additional amount of trityl chloride (3.3 g) is charged on the second and third days. The reaction is monitored by thin layer chromatography on silica gel plates using a mixture of chloroform and ethanol (10:1 v/v) as the developing solvent. After all the starting material is consumed, the mixture is concentrated in vacuo, and the residue coevaporated several times with toluene and ethanol, and then chromatographed on a silica column using chloroform-ethanol (19:1 v/v) as the eluent to give 5'-O-trityl-1-benzylinosine which is crystallized from ethanol: 5.40 g (90% yield), mp 208°-209° C. 1H NMR (Me2 SO-d6) δ 3.20-3.24 (2H, m, H-5',5"), 4.10-4.29 (2H, m, H-3',4'), 4.61-4.67 (1H, m, H-2', collapsed to dd upon addition of D2O, J1',2' =5.6, J2',3' =5.0 Hz), 5.24 (2H, s, CH2Ph), 5.21-5.27 (1H, m, OH, exchangeable), 5.57 (1H, d, OH), 5.92 (1H, d, H-1'), 7.06-7.32 (20H, m, Tr, CH2Ph), 8.23, 8.51 (1H each, H-2, H-8). Analyses: calculated for C26H32N4O5 : C, 71.98, H, 5.37, N, 9.33. Found: C, 71.86, H, 5.44, N, 9.18.

Provenance & Evidence