4-Toluenesulfonyl chloride → 1-(3,5-Di-o-benzyl-2,6-di-o-(p-toluenesulphonyl)-beta-d-allofuranosyl)thymine

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Reaction Steps

To a stirred solution of nucleoside 16 (0.60 g, 1.28 mmol) in dichloromethane (70 cm3) at room temperature was added 4—N,N-(dimethylamino)pyridine (0.63g, 5.12 mmol) and p-toluenesulphonyl chloride (0.73 g, 3.84 mmol). After stirring for 3 h, ice-cold H2O (50 cm3) was added and extraction was performed using dichloromethane (3×75 cm3). The combined organic phase was dried (Na2SO4) and evaporated to dryness under reduced pressure. The residue was purified by silica gel column chromatography using dichloromethane/methanol (99.5:0.5, v/v) as eluent to give nucleoside 17 as white solid material (0.71 g, 71%) after evaporation of the solvents under reduced pressure.

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