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

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Reaction Steps

To a solution of 3.64 g (10 mmol) of the 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester produced in Example 26 in methanol (36 mL) was added 10 mL of 1N-aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 2 hours. This reaction mixture was adjusted to pH 7 by gradual addition of 1N-hydrochoric acid under ice-cooling. The methanol was then distilled off under reduced pressure and the residual aqueous solution was extracted with 2 portions of methylene chloride, 70 mL each. The organic layer was dehydrated over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give a colorless oil. This residue was purified by silica gel column chromatography (Kieselgel 60, product of Merck; hexane:acetone=5:1) to give 2.34 g of 2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic tert-butyl ester (white solid). Yield 90%.

Provenance & Evidence