(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → N-Methyl-D-glucamine

Participants

Reaction Steps

20 g of amphotericin B and 6 g of glucose was dissolved in 200 ml of dimethyl formamide and allowed to stand at a temperature of 35° C. for 18 hours. The resulting solution was filtered and 500 ml of 5% ammonium sulphate, aqueous solution, was added to the filtrate the mixture was then allowed to stand at a temperature of +40° C. for 2 hours. The precipitate was filtered and washed with water. 1500 ml of methanol at a temperature of 50° C. and 6 g of N-methylglucamine salt dissolved in 60 ml of water was added to the precipitate whereupon the mixture was stirred for 30 minutes, then 1 l of n-butanol was added. The resulting solution was evaporated at a temperature of 45° C. under reduced pressure until the methanol and water were removed. The residue was allowed to stand at a temperature of +4° C. for crystallization. The sediment was filtered, washed with n-butanol then with petroleum ether and dried at the room temperature. 18 g of the N-methylglucamine salt of N-glycosyl derivative of amphotericin B of E1 cm1% =1140 at 380 nm and IC50 =0.1 mcg/ml were obtained.

Provenance & Evidence