(3-(Trifluoromethyl)phenyl)hydrazine → Sophorose

HRID 1653935Notes

Reaction equation

HRID 1653935 reaction equation
C([O-])(=[O:3])C.[Na+].FC(F)(F)C1C=C(NN)C=CC=1.[O:18]=[CH:19][C@@H:20]([C@H:22]([C@@H:24]([C@@H:26]([CH2:28][OH:29])[OH:27])[OH:25])[OH:23])[OH:21].FC(F)(F)C1C=C(NN=[CH:40][C@@H:41]([C@H:43]([C@@H:45]([C@@H:47]([CH2:49][OH:50])O)[OH:46])[OH:44])[OH:42])C=CC=1>O>[C@@H:28]1([O:29][C@H:47]([C@H:45]([C@@H:43]([C@@H:41]([CH2:40][OH:3])[OH:42])[OH:44])[OH:46])[CH:49]=[O:50])[O:21][C@H:20]([CH2:19][OH:18])[C@@H:22]([OH:23])[C@H:24]([OH:25])[C@H:26]1[OH:27]

Participants

6

Reactant 4

HCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 517045Sodium AcetateHCID 86748606D-glucose 3-(trifluoromethyl)phenyl hydrazone

Product 1

HCID 92797Sophorose

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To this oligosaccharide (10 μmol), sodium acetate (30 μmol) in a small vial (Pierce reacti-vial, 0.2 mL capacity, with Tuf-bond Teflon-silicone cap seals) was added 150 μL water. 3-(trifluoromethyl)phenylhydrazine (40 μmol, Aldrich) was added, the sample sealed under nitrogen, and heated to 90° C. for 48 hours. The oligosaccharide was converted (>98%) to D-glucose and D-glucose 3-(trifluoromethyl)phenyl hydrazone, in a 1:2 ratio.

Workup

  1. customthe sample sealed under nitrogen

Sources & evidence

ORD record
ord-497474b42c1c45b88ea6d1649eb81a59
Source dataset
uspto-grants-1995_04
Patent number
US05403927

Reaction notes

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