反应详情

The formed substance, 3,4-di-O-allyl-5,6-di-O-benzyl-myo-inositol (12.1 g) together with dibutylin oxide (4.0 g) and dry benzene (150 ml) was heated under reflux for 2 hours. After evaporation of benzene and addition of dry dimethyl formamide (60 ml) and benzyl bromide (5.5 ml) the solution was kept at 50° C. for 24 hours. The crude product was chromatographed on silica gel (250 g) and eluted with ether-light petroleum to give 9.5 g of 1,5,6-tri-O-benzyl-3,4-di-O-allyl-myo-inositol. A mixture of the obtained product, toluene-p-sulphonic acid monohydrate (0.9 g), ethanol (190 ml), water (10 ml) and palladium-on-charcoal (1 g, 10% from Fluka) was heated under reflux with stirring for 4 hours. The crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1) gave a compound, identified with NMR to be 1,5,6-tri-O-benzyl-myo-inositol. The described substances are racemic mixtures. If desired the racemic mixture of the latter one could be separated into the enantiomeric forms by forming diastereomers with camphanic acid.

1. temperaturewas heated
2. temperatureunder reflux
3. customThe crude product was chromatographed on silica gel and elution with ether-light petroleum (4:1)
4. customgave a compound
5. additionthe racemic mixture of the latter one
6. customcould be separated into the enantiomeric forms