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

HRID 1701789Notes

Reaction equation

HRID 1701789 reaction equation
C[C@@H]1[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@@]2(O)O[C@H]([C@H](C(O)=O)[C@@H](O)C2)C[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H:58]([NH2:64])[C@H]2O)C=CC=CC=CC=CCCC=CC=C1.[O:66]=[CH:67][C@@H:68]([C@H:70]([C@H:72]([C@@H:74]([CH2:76]O)[OH:75])[OH:73])[OH:71])[OH:69]>CN(C)C=O>[CH3:58][NH:64][CH2:76][C@@H:74]([C@H:72]([C@@H:70]([C@@H:68]([CH2:67][OH:66])[OH:69])[OH:71])[OH:73])[OH:75]

Participants

4

Reactant 2

HCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 444248381400-61-9

Product 1

HCID 8567N-Methyl-D-glucamineYield 398.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of nystatin and 1.5 g of galactose were suspended in 50 ml of dimethyl formamide and next the procedure was carried out as in Example IV. 4.2 g of N-methylglucamine salt of N-glycosyl nystatin of E1 cm1% =600 at 304 nm and IC50 =0.45 mcg/ml were obtained. Original antibiotic: E1 cm1% =790 at 304 nm, IC50 =0.18 mcg/ml.

Sources & evidence

ORD record
ord-757915982b4042059b6ccfdbb602b181
Source dataset
uspto-grants-1980_03
Patent number
US04195172

Reaction notes

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