Sodium Bicarbonate → HCID 70377649, compound

Participants

Reaction Steps

A solution of 600 mg (1.82 mmol) of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline of the formula ##STR13## [prepared according to V. K. Srivastava, Carbohydrate Research 103, 286 (1982)]and 605 mg (3.64 mmol) of glycolic acid benzyl ester in 6 ml of methylene chloride is added to a solution of 300 mg (1.85 mmol) of iron(III) chloride (anhydrous) in 6 ml of absolute methylene chloride and the whole is stirred for 21 hours at 22°. 8 ml of cold, saturated sodium bicarbonate solution are added and the mixture is diluted with 100 ml of chloroform and filtered until clear. The organic phase of the filtrate yields, after drying over magnesium sulphate and concentration by evaporation, a yellow oil which is purified by digesting an ethyl acetate solution with hexane and by chromatography on silica gel. 2-(2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)-acetic acid benzyl ester is obtained in the form of a colourless powder.

Provenance & Evidence