Chloroform → 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride

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Reaction Steps

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was prepared as follows. 2-Acetamido-2-deoxy-D-glucose (50 g, 0.226 mol) was added to chilled acetyl chloride (125 ml). The mixture was then stirred at room temperature for 16 hr. Chloroform (300 ml) was added to the reaction mixture through the condenser and the resulting homogeneous solution was added to a vigorously stirred solution of 400 grams of ice and 100 ml of water. The organic layer was separated, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. This filtrate was concentrated to about 75 ml under reduced pressure. Ether (400 ml) was added to the concentrated solution and left at room temperature for 2 hr to give the product as a white solid. This white solid was filtered and dried in a vacuum desiccator over sodium hydroxide and phosphorous pentoxide to give 52.5 grams of the title cmp. M.p. 123°-125° C.

Provenance & Evidence