Sodium Methoxide → 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-(2-methoxyethyl)-9H-purine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 9-[(3aR,4R,6R,6aR)-6-({[tert-butyl(dimethyl)silyl]oxy}-methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-vinyl-9H-purine (100 mg, 0.23 mmol) in DCM (5.0 mL) was added NaOMe (0.5M in MeOH, 4.6 mL, 2.2 mmol) at 0° C. The reaction was stirred for 2 h at 0° C. and r.t. overnight. The mixture was diluted with DCM and washed with saturated aq NH4Cl. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 10% MeOH/DCM) to yield 70 mg (66%) of the title compound.

Provenance & Evidence