Ethyl Acetate → GlyTouCan:G58715BY

HRID 1491952Notes

Reaction equation

HRID 1491952 reaction equation
C([O:4][C@@H:5]1[O:22][C@@H:21]([CH3:23])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(O)(=O)C.NN.C(OCC)(=O)C>CN(C)C=O>[C:8]([O:7][C@H:6]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:21]([CH3:23])[O:22][CH:5]1[OH:4])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 165591Hydrazine, acetate (1:1)HCID 110888731,2,3,4-Tetra-O-acetyl-a-L-fucopyranose

Product 1

HCID 10979132GlyTouCan:G58715BYYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,2,3,4-tetra-O-acetyl-α-L-fucopyranose (6.00 g, 18 mmol), prepared, for example, according to Nunez et al., supra., and hydrazine acetate (1.99 g, 21.6 mmol) in 20 ml of dry dimethylformamide is stirred at 50° C. for 4.5 h. After addition of ethyl acetate, the mixture is extracted about twice with aqueous sodium chloride solution and the concentrated organic extract is chromatographed (petroleum ether (40°-60°)/ethyl acetate 1:1). 2,3,4-Tri-O-acetyl-L-fucopyranose (1) is obtained in an anomer ratio of α:β of 3:1 with a yield of 80%. TLC analysis (petroleum ether (40°-60°)/ethyl acetate 1:1) gives Rf =0.47.

Workup

  1. extractionthe mixture is extracted about twice with aqueous sodium chloride solution
  2. extractionthe concentrated organic extract
  3. customis chromatographed (petroleum ether (40°-60°)/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-1a10c28ccb584ca5831b52141f8217c2
Source dataset
uspto-grants-1994_12
Patent number
US05371203

Reaction notes

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