L-Gulose → Anhydro-d-mannosan

HRID 728206Notes

Reaction equation

HRID 728206 reaction equation
O=[CH:2][C@H:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]>O>[C@@H:11]12[O:12][CH2:2][C@H:3]([O:4]1)[C@@H:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]2[OH:10]

Participants

3

Reactant 1

HCID 80127L-Gulose

Product 1

HCID 11947765Anhydro-d-mannosan

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Syrupy L-gulose was heated on a steam bath in water with strong acid resin (Dowex 50 W-X8, H+ form) for 64 h. The solution was then filtered, the resin washed with water, and the combined filtrate was passed onto a column packed with strong base resin (Amberlite IRA-900, OH- form). The column was washed with distilled water to elute the title compound which crystallized from ethanol. Recrystallized from ethanol it has mp 155.5°-156.5° C. The column was then immediately washed with aqueous acetic acid (M) to elute unreacted L-gulose which was recycled to provide further title compound.

Workup

  1. filtrationThe solution was then filtered
  2. washthe resin washed with water
  3. washThe column was washed with distilled water
  4. washto elute the title compound which
  5. customcrystallized from ethanol
  6. customRecrystallized from ethanol it
  7. washThe column was then immediately washed with aqueous acetic acid (M)
  8. washto elute unreacted L-gulose which

Sources & evidence

ORD record
ord-7071e9fa7c1e442a8c0394816aa747f6
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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