HCID 10006646, compound → 5-Amino-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

Participants

Reaction Steps

An aqueous solution (30 mL) of validamycin G (106 mg) was submitted to catalytic reduction at room temperature under atmospheric pressure in the presence of platinum oxide (10 mg). The catalyst was removed by filtration and the filtrate was adsorbed onto a column of Amberlite CG-50 (NH4+ form, 30 mL) followed by washing with water and then elution with 0.5N aqueous ammonia. The eluate was concentrated to dryness under reduced pressure, and the residue was dissolved in 1N sulfuric acid (20 mL) and hydrolyzed at 80° C. for 10 hours. The reaction mixture was neutralized with barium hydroxide and the supernatant obtained by centrifugation was concentrated under reduced pressure. The concentrate was adsorbed onto a column of Amberlite CG-50 (ammonium form, 20 mL) followed by washing with water and then elution with 0.5N aqueous ammonia. The eluate was concentrated under reduced pressure and submitted to column chromatography on Dowex 1×2 (OH- form, 100 mL) followed by elution with water. The eluate fractions were concentrated under reduced pressure and then freeze-dried, to give a white powder of valiolamine (11 mg).

Provenance & Evidence