Potassium Carbonate → HCID 69710311, compound

Participants

Reaction Conditions

Reaction Steps

A mixture that consists of 46.25 g (100 mmol) of 2,3,5-tri-O-benzoylribofuranose, 1.39 g (5 mmol) of tetrabutylammonium chloride in 400 ml of methyl-tert-butyl ether, and 82.93 g (600 mmol) of potassium carbonate is cooled to 0° C. At 0° C., 22.91 g (150 mmol) of bromoacetic acid benzyl ester is added in drops over 20 minutes while being stirred vigorously. It is stirred for one hour at 0° C. 500 ml of methyl-tert-butyl ether is added thereto, the organic phase is separated, and the aqueous phase is extracted twice with 200 ml of methyl-tert-butyl ether. The solvent of the combined organic phases is dried on sodium sulfate, dessicant is filtered out and distilled off in a vacuum. The residue is taken up in 500 ml of ethanol. 5 g of palladium (10%) on activated carbon is added thereto, and it is hydrogenated until hydrogen absorption is completed. Then, catalyst is filtered out, it is rewashed with a little ethanol and evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/nhexane/ethanol/acetic acid=20:5:3:0.5). The product-containing fractions are concentrated by evaporation, dissolved in 200 ml of ethyl acetate and shaken out three times with 200 ml of water. Then, the organic phase is separated and evaporated to the dry state in a vacuum.

Provenance & Evidence