D-(-)-Fructose → N-Methyl-D-glucamine

HRID 1701788Notes

Reaction equation

[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)[OH:10])[OH:8])[OH:6])=[O:4].[CH3:13][N:14](C)C=O>>[CH3:13][NH:14][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

Reactant 2

HCID 5984D-(-)-Fructose

HCID 6228Dimethylformamide

Product 1

HCID 8567N-Methyl-D-glucamine

Procedure

5 g of polifungin and 1.5 g of fructose were suspended in 50 ml of dimethyl formamide and next the procedure was carried out as in the Example IV. 4.4 g of N-methylglucamine salt of N-glycosyl polifungin of E1 cm1% =562 at 304 nm and IC50 =0.46 mcg/ml were obtained. Original antibiotic: E1 cm1% =660 at 304 nm and IC50 =0.16 mcg/ml.

Sources & evidence

ORD record: ord-17b52b957d2149a6b471a58baa285d61
Source dataset: uspto-grants-1980_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04195172

Reaction notes

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