Tetrabutylammonium Fluoride → N-Benzoyl-3'-O-[bis(4-methoxyphenyl)(phenyl)methyl]-2'-deoxyadenosine

Participants

Reaction Steps

N6-benzoyl-5′-O-(tert-butyldimethylsilyl)-3′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine (16.2 g) was dissolved in 200 ml of dry THF. A THF solution (31 ml) of tetrabutylammonium fluoride was added to the resultant solution and 100 ml of dry THF was further added, followed by stirring at room temperature. After 8 hours, THF was distilled off and extraction using chloroform was carried out. The extract was then washed by a saturated solution of sodium chloride and dried with anhydrous magnesium sulfate. The extract was then concentrated and purified by column chromatography (ethyl acetate/hexane/methanol) to obtain 13.8 g of the titled compound as a white powder (yield: 98%).

Provenance & Evidence