HCID 21123040, compound → L-(-)-Fucose
Reaction equation
[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4]>O.[O-][Mo]([O-])(=O)=O>[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 78 °C
Procedure
The resin-supported molybdate obtained above (10 g) was added to a mixture of 6-deoxy-L-talose (10 g) in water (40 ml). The reaction mixture was stirred at 78° C. (inside the reactor). After cooling to rt the mixture was filtered, the filtrate passed through a column of IRA 400 resin (5 g, OH form, d=1 cm, l=5 cm) two times and concentrated. The residue was dissolved in isopropanol (40 ml) and directly evaporated. Isobutanol (50 ml) was added and the mixture was heated to reflux for 10 min. and allowed to cool. Crystallization spontaneously occurs or it was promoted by adding seed crystals. After 6 h at room temperature the suspension was filtered to give L-fucose (5.4 g, 54%).
Workup
- temperatureAfter cooling to rt the mixture
- filtrationwas filtered
- concentrationconcentrated
- dissolutionThe residue was dissolved in isopropanol (40 ml)
- customdirectly evaporated
- additionIsobutanol (50 ml) was added
- temperaturethe mixture was heated
- temperatureto reflux for 10 min.
- temperatureto cool
- customCrystallization
- additionby adding seed crystals
- filtrationAfter 6 h at room temperature the suspension was filtered
Sources & evidence
- ORD record
- ord-af1b876f2ada478796445625590bc8ae
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901291B2
Reaction notes
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