Boron trifluoride etherate → HCID 68582071, compound

Participants

Reaction Steps

1-O-Acetyl-2-C-methyl-2,3,5-tri-O-benzoyl-D-ribofuranose (1.0 g, 1.72 mmol) was dissolved in anhydrous nitromethane (10.0 mL) and to this solution compound 1.2 (312 mg, 1.21 mmol) was added. The resulting suspension was brought to reflux and borontrifluoride etherate (0.23 mL, 1.78 mmol) was added. The suspension became a clear solution, which was heated at reflux for 2 hr. The mixture was cooled, the solvents were evaporated and the off-white foamy residue was dissolved in ethyl acetate and then poured with stirring into aq. sat. NaHCO3. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were dried (Na2SO4), filtered and evaporated to give an off-white solid. This material was purified by flash column chromatography on silica gel using CH2Cl2 to 2-3% MeOH in dichoromethane as eluent to give the desired compound 1.4 (811 mg) as a yellow foam.

Provenance & Evidence