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: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
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
MoO3 (600 mg) was added to a mixture of 6-deoxy-L-talose (100 g) in water (1.5 l). The reaction mixture was stirred for 9.5 h at reflux. At 80° C. resin IRA-67 (SUPELCO, 50 g) was added and the mixture was stirred for further 30 min, filtered and distilled off. The residue was dissolved in isopropanol (400 ml) and directly evaporated. Isobutanol (400 ml) was then added and the mixture was heated under reflux for 10 min and allowed to cool. Crystallization spontaneously occurs or it was promoted by adding seed crystals. After one night at room temperature the suspension was filtered to give L-fucose (52 g, 52%).
Workup
- temperatureat reflux
- customAt 80° C.
- addition(SUPELCO, 50 g) was added
- stirringthe mixture was stirred for further 30 min
- filtrationfiltered
- distillationdistilled off
- dissolutionThe residue was dissolved in isopropanol (400 ml)
- customdirectly evaporated
- additionIsobutanol (400 ml) was then added
- temperaturethe mixture was heated
- temperatureunder reflux for 10 min
- temperatureto cool
- customCrystallization
- additionby adding seed crystals
- filtrationAfter one night at room temperature the suspension was filtered
Sources & evidence
- ORD record
- ord-391d687b0df3409bb195ec9466b0def5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901291B2
Reaction notes
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