Trifluoromethanesulfonic acid → HCID 86595232, compound

Participants

Reaction Conditions

Reaction Steps

In 35 mL of chloroform were dissolved 2.4 g of benzyl 2-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosylthio)ethylcarbamate and 1 g of methyl 3-hydroxy-2-(octadecanoylamino)propionate, and after cooling the solution to 0° C., 1.4 g of N-iodosuccinimide and 0.13 mL of trifluoromethanesulfonic acid were added to the solution and the resulting mixture was stirred at room temperature for 3 hours. Then, chloroform was added to the reaction mixture, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution and 10% aqueous sodium thiosulfate solution. The chloroform layer was dried over anhydrous magnesium sulfate, magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (Eluent; n-hexane:ethyl acetate=3:1) to obtain 1.4 g of methyl 2-(octadecanoylamino)-3-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyloxy)propionate.

Provenance & Evidence