Imidazole → 6-O-(4,4'-dimethoxytrityl)-3-O-(2-fluoroethyl)-4-O-(triethylsilyl)-2-deoxy-2-(thymin-1yl)-D-altro-hexitol

Participants

Reaction Steps

Compound 6, prepared as per the procedures illustrated in Example 13 (2.50 g, 4.00 mmol) was mixed with imidazole (1.36 g, 20.0 mmol) over P2O5 under reduced pressure. This mixture was dissolved in anhydrous DMF (13 mL) and chloro triethylsilane (1.71 mL, 10 mmol) was added. The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted in EtOAc (100 mL), washed with sat. NaHCO3 (100 mL) and brine (50 mL) then dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (50% EtOAc in hexanes) to yield Compound 8 (2.45 g, 82.5%) as a white foam. MS (ES): m/z 760.2 [M+Na]+.

Provenance & Evidence