1-(Hydroxymethyl)-5-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}cyclohexane-1,2,3,4-tetrol → 5-Amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

Participants

Reaction Steps

An aqueous solution (50 mL) of validoxylamine G (420 mg) was submitted to catalytic reduction at room temperature under atmospheric pressure in the presence of platinum oxide (20 mg). The catalyst was removed by filtration, and the filtrate was adsorbed onto a column of Amberlite CG-50 (NH4- form, 50 mL) followed by washing with water and then elution with 0.5N aqueous ammonia (200 mL). The eluate was concentrated under reduced pressure, and submitted to column chromatography on Dowex 1×2 (OH- form, 100 mL) and eluted with water. The eluate fractions (120-200 mL) were concentrated to dryness under reduced pressure, to give white powders of valiolamine (60 mg).

Provenance & Evidence