Tetrabutylammonium Fluoride → {9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate

Participants

Reaction Steps

{9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl methanesulfonate (240 mg, 0.3 mmol) (preparation 16) was dissolved in stirred tetrahydrofuran (1 ml) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.6 ml, 0.6 mmol) added. The reaction mixture was stirred at room temperature for 24 hr. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (95:5) increasing in polarity to dichloromethane:methanol (90:10). This gave the title compound (140 mg) as a foam. MS: 570 (MH+).

Provenance & Evidence