Ethyl Acetate → (E)-2-(acetoxy-methyl)-6-(4-(3,5-dimethoxystyryl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of acetobromo-α-D-glucose (48 mg, 0.11 mM) and benzyltriethylammonium bromide (13 mg, 0.04 mM) in chloroform was added a solution of pterostilbene (30 mg, 0.11 mM)) in 1.25 M (2.5 mL) of NaOH. The mixture was stirred at 60° C. for 5 h and after a second addition of 10 mg of acetobromo-α-D-glucose and 1.0 mL of NaOH) the mixture was stirred at 60° C. for additional 5 h. Ethyl acetate was added and the organic phase was washed with water. The crude mixture was purified using flash chromatography eluting with ethyl acetate/hexanes (3:2) and afforded (E)-2-(acetoxy-methyl)-6-(4-(3,5-dimethoxystyryl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate.

Provenance & Evidence