Acetonitrile → Ethyl acetate hexane

Participants

Reaction Steps

(3S,4S,5E,8S)-4,8-dimethyl-9-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]non-5-en-3-ol (190 mg, 0.50 mmol) was dissolved in acetonitrile (7.5 ml) and 0.05M sodium tetraborate decahydrate −0.4 mM disodium ethylenediaminetetraacetate salt solution (5 ml). 1,2:4,5-di-O-isopropylidene-D-erythro-2,3-hexodiuro-2,6-pyranose (450 mg, 1.74 mmol) was added while ice cooling. Subsequently, a mixed powder of potassium carbonate (0.85 mg, 6.16 mmol) and oxone (1.27 g, 2.06 mmol) was added at the same temperature over one hour. The reaction solution was stirred at the same temperature for further one hour. The reaction solution was diluted with ethyl acetate and washed with water and brine. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto, commercial name Silica Gel 60N, 40-100 μm; heptane:ethyl acetate=3:1) to obtain the title compound (160 mg, 94% ee) as a colorless oil. The optical purity was determined by HPLC using a chiral column (DAICEL, commercial name CHIRALCEL OD; n-hexane:isopropyl alcohol=75:25).

Provenance & Evidence