beta-Maltose → N-Methyl-D-glucamine

HRID 1701790Notes

Reaction equation

HRID 1701790 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.[CH2:66](O)[C@H:67]1[O:72][C@H:71]([O:73][C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H:70]([OH:85])[C@@H:69]([OH:86])[C@@H:68]1[OH:87]>CN(C)C=O>[CH3:58][NH:64][CH2:66][C@@H:67]([C@H:68]([C@@H:69]([C@@H:70]([CH2:71][OH:73])[OH:85])[OH:86])[OH:87])[OH:72]

Participants

4

Reactant 2

HCID 6255beta-MaltoseHCID 444248381400-61-9

Product 1

HCID 8567N-Methyl-D-glucamineYield 427%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of nystatin and 3.0 g of maltose were suspended in 50 ml of dimethyl formamide and next the procedure was carried out as in Example IV. 4.5 g of N-methylglucamine salt of N-glycosyl nystatin of E1 cm1% =580 at 304 nm and IC50 =0.45 mcg/ml were obtained. Original antibiotic exhibited: E1 cm1% =790 at 304 nm and IC50 =0.18 mcg/ml.

Sources & evidence

ORD record
ord-dc1ac723d53c486abc1cf5010f12e1e9
Source dataset
uspto-grants-1980_03
Patent number
US04195172

Reaction notes

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