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

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.

1. filtrationThe resulting solution was filtered
2. addition500 ml of 5% ammonium sulphate, aqueous solution, was added to the filtrate the mixture
3. waitto stand at a temperature of +40° C. for 2 hours
4. filtrationThe precipitate was filtered
5. washwashed with water
6. dissolution1500 ml of methanol at a temperature of 50° C. and 6 g of N-methylglucamine salt dissolved in 60 ml of water
7. additionwas added to the precipitate whereupon the mixture
8. addition1 l of n-butanol was added
9. customThe resulting solution was evaporated at a temperature of 45° C. under reduced pressure until the methanol and water
10. customwere removed
11. customto stand at a temperature of +4° C. for crystallization
12. filtrationThe sediment was filtered
13. washwashed with n-butanol
14. dry with materialwith petroleum ether and dried at the room temperature

ORD record

ord-8c3b1defac4b489d8b22cd67882bbc4b

Source dataset

uspto-grants-1980_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04195172