Tin tetrachloride → HCID 23270450, compound

Participants

Reaction Steps

Dried (2R)-5,7,3′,4′-tetrakis(methyloxy)flavan-3-one (1) (200 mg, 0.581 mmol) and (2R,3S)-5,7,3′,4′-tetrakis(methyloxy)flavan-3-ol (5) (400 mg, 1.162 mmol, 2 eq.) was dissolved in dry dichloromethane (10 mL) and the mixture was cooled in ice/NaCl bath. Then tin(IV)chloride (1 M solution in dichloromethane, 1 mL, 1 mmol, 1.7 eq.) was added dropwise and the reaction mixture was stirred under argon in thawing ice/NaCl bath for 24 hours (TLC monitoring of consumption of starting materials). The reaction mixture was then filtered on a basic aluminium oxide and washed with ethyl acetate. Purification on silica preparative TLC plates (hexane-ethyl acetate 4:6) afforded (2R)-3-[(2R,3S)-5,7,3′,4′-tetrakis(methyloxy)-3-hydroxyflavan)]-5,7,3′,4′-tetramethoxyflavan-3-ene (6) (Rf 0.20, 40.1 mg, 0.060 mmol, 10%).

Provenance & Evidence