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

HRID 1397651Notes

Reaction equation

HRID 1397651 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

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

  1. temperatureat reflux
  2. customAt 80° C.
  3. addition(SUPELCO, 50 g) was added
  4. stirringthe mixture was stirred for further 30 min
  5. filtrationfiltered
  6. distillationdistilled off
  7. dissolutionThe residue was dissolved in isopropanol (400 ml)
  8. customdirectly evaporated
  9. additionIsobutanol (400 ml) was then added
  10. temperaturethe mixture was heated
  11. temperatureunder reflux for 10 min
  12. temperatureto cool
  13. customCrystallization
  14. additionby adding seed crystals
  15. 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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