tert-Butyl hydroperoxide → HCID 10973444, compound

Participants

Reaction Conditions

Reaction Steps

t-Butylhydroperoxide in decane (5M, 0.45 ml) was added to a solution of methyl 6-[(1R,4R,5S,6R)-6-(tert-butyloxycarbonylamino)-4,5-dihydroxy-2-cyclohexen-1-yl]-4-(phenylmethoxy)-1,3-benzodioxole-5-carboxylate (280 mg, 0.55 mmol) and vanadyl acetylacetonate (7 mg, 0.026 mmol) in benzene (10 ml). After stirring for 2 h at 60° C, the reaction mixture was concentrated under reduced pressure and subjected to chromatography (hexane/ethyl acetate, 1:5) to afford 129 mg (53%) of epoxide 16 and 42 mg of recovered starting material. 1H NMR (270 MHz, CDCl3) ε 7.27~7.40 (m, 5H), 7.04 (s, 1H), 5.99 (d, J=2.3 Hz, 2H), 5.68 (bd, J=7.3 Hz, 1H), 5.24 (AB, J=11.3 Hz, Δν=16.5 Hz, 2H), 4.28 (t, J=4.99 Hz, 1H), 3.83 (m, 4H), 3.35~3.46 (m, 3H), 3.07 (d, J=10.9 Hz, 1H), 1.33 (s, 9H).

Provenance & Evidence