Potassium Bromide → tert-Butyl 3,5-dideoxy-2,4-O-(1-methylethylidene)-L-erythro-hexuronate

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Reaction Steps

2,2,6,6-tetramethyl piperidinyl oxy free radical (TEMPO) (0.2 g), potassium bromide (9.6 g) and sodium bicarbonate (90 g) were dissolved in methylene chloride (600 ml) and stirred the contents together at 0–5° C. A solution of (4R-cis)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester of Formula III (100 g) in methylene chloride (400 ml) was added to the above solution at 0–5° C. To this solution 10% sodium hypochlorite solution (159 ml) (NaOCl) was added at 0–5° C. Again sodium bicarbonate (96 g) and followed by 10% sodium hypochlorite solution was added to the reaction mass. Reaction mass was maintained for 1–2 hours at 0–5° C. and filtered through perlite. The organic layer was separated and washed with 10% sodium thiosulfate solution (250 ml), then water (250 ml) followed by saturated sodium chloride solution (250 ml). Organic layer was distilled at below 40° C. under reduced pressure to afford the title product. Yield: 95 g.

Provenance & Evidence