Imidazole → N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamide

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Reaction Steps

N6-benzoyl-2′-deoxyadenosine (20.95 g ) was dissolved in 200 ml of DMF. Imidazole (15.7 g) was dissolved to the resultant solution by addition. Then, 20.8 g of tert-butyldimethylsilyl chloride was added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction using chloroform was carried out and the organic layer was washed by a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After concentration of the extract, the target compound was purified by column chromatography (methanol/chloroform) to obtain 16.1 g of the titled compound (yield; 61%).

Provenance & Evidence