Potassium Carbonate → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

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Reaction Steps

In 100 mL of methanol was dissolved 10 g (33.1 mmol) of tert-butyl 2-{(4R,6S)-2,2-dimethyl-6-[(methylcarbonyloxy)methyl]-1,3-dioxan-4-yl}acetate [synthesized by the process described in Example 8], and under ice-cooling and stirring, 0.46 g (3.3 mmol) of potassium carbonate was added. The mixture was further stirred under ice-cooling for 4 hours. From this reaction mixture, the reaction solvent was distilled off by heating under reduced pressure, and the residue was diluted with 50 mL of water and neutralized with 0.1 N-hydrochloric acid. This solution was extracted with ethyl acetate and the resulting organic layer was washed with water and dehydrated over anhydrous sodium sulfate. The solvent was then distilled off by heating under reduced pressure. The oily residue was decompressed to 1 Torr or less with a vacuum pump to remove the solvent almost thoroughly. As a result, 8.6 g of tert-butyl 2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate (colorless oil) was obtained in a yield of 100%.

Provenance & Evidence