Sucrose → HCID 14061412, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100 ml of 0.1 M phosphate buffer (pH 7) containing sucrose (15 g) was dispersed 7.0 g of baker's yeast at 30° C., and the mixture was shaken at 30° C. for 15 minutes. To the resulting mixture was added an emulsion of 505 mg of (1SR,5RS)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one (VIII) in 0.2% Triton X-100 solution (15 ml), and the mixture was shaken at 30° C. After 8 hours, 10 g of sucrose were added to the mixture. After shaking for 24 hours, the reaction mixture was filtered through Celite, the filtrate was saturated with sodium chloride and extracted three times with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (eluting solution: 20% (v/v) diethyl ether/hexane) to obtain 183 mg of oily (1S,5R)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one, (IV).

Provenance & Evidence