1-Propanol → N-Methyl-D-glucamine

HRID 1701786Notes

Reaction equation

HRID 1701786 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)[OH:10])[OH:8])[OH:6])[OH:4].CCCCCO.C(O)CC.[CH3:23][N:24](C)C=O>O>[CH3:23][NH:24][CH2:11][C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10]

Participants

6

Reactant 4

HCID 10311-PropanolHCID 6228DimethylformamideHCID 62761-PentanolHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 8567N-Methyl-D-glucamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 g of polifungin and 6 g of glucose were dissolved in 100 ml of dimethyl formamide and then the procedure was carried out as in the Example V, but instead of n-amyl alcohol there was used n-propyl alcohol in the same quantity as n-amyl one. 16.0 g of N-methylglucamine salt of N-glycosyl polifungin, soluble in water, of biological activity of 2010 U/mg, E1 cm1% =558 at 304 nm were obtained. Original antibiotic: E1 cm1% =720 at 304 nm.

Sources & evidence

ORD record
ord-7307a136b4e14338b0be6f4cd5f4f192
Source dataset
uspto-grants-1980_03
Patent number
US04195172

Reaction notes

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