(R)-(+)-Glycidol

Typical procedure (Synthesis of the glycol thymine nucleoside (2)): To a solution of (R)-glycidol (1.0 mL) and Et3N (5.4 mL) in CH2Cl2 (34 mL) was added DMTrCl (6.45 g). After 12 h, the reaction mixture was poured into sat. NaHCO3 (50 mL). The organic layer was evaporated; the residue was dissolved in EtOAc, washed with sat. NaHCO3, and purified by silica gel chromatography (elute: hexane/EtOAc/Et3N = 10/1/0.01) to give the DMTr-glycidol (1) as an oil (5.98 g, quant.). A mixture of thymine (0.63 g) and NaH (60 % dispersion in paraffin liquid, 42 mg) in DMF (8 mL) was stirred at rt for 2 h. The DMF (10 mL) solution of the DMTr-glycidol (1) (1.79 g) was added, and the resulting mixture was heated at 110 °C for 20 h. The DMF was evaporated, the residue was extracted with EtOAc, and purified by silica gel chromatography (elute: hexanes/EtOAc/Et3N = 1/2/0.01) to give the glycol thymine nucleoside (2) as a colorless foam (1.22 g, 49 %).