Tetrabutylammonium Fluoride → 2'-Deoxy-3'-O-DMT-N2-Isobutyrylguanosine

Participants

Reaction Steps

N2-isobutyryl-5′-O-(tert-butyldimethylsilyl)-3′-O-(4,4′-dimethoxytrityl)-2′-deoxyguanosine (25 g) was dissolved in 200 ml of dry THF. A THF solution (40 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, extraction using chloroform was carried out, and the extract was 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 12.9 g of the titled compound as a white powder (yield: 60%).

Provenance & Evidence