HCID 21123040, compound → L-(-)-Fucose

HRID 1397652Notes

Reaction equation

HRID 1397652 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

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

  1. temperatureAfter cooling to rt the mixture
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in isopropanol (40 ml)
  5. customdirectly evaporated
  6. additionIsobutanol (50 ml) was added
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 10 min.
  9. temperatureto cool
  10. customCrystallization
  11. additionby adding seed crystals
  12. 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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