L-Gulose → Anhydro-d-mannosan

Participants

Reaction Steps

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.

Provenance & Evidence