m-Chloroperbenzoic acid → (1R,2R,3S,5S)-3-(Hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

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Reaction Steps

To a solution of (1S,5S)-5-(hydroxymethyl)cyclopent-2-en-1-ol (3.19 g, 27.9 mmol) (An, G.-I.; Rhee, H. Nucleosides Nucleotides 2002, 21, 65-72) in DCM (143 mL) at 0° C. was added 3-chloroperbenzoic acid (7.52 g, 33.5 mmol) and the mixture was stirred at room temperature for 4 hours. Silica gel (20 g) was added, the mixture was concentrated to dryness and was purified via flash chromatography (0 to 100% EtOAc/DCM) to afford the title compound (2.75 g, 76%).

Provenance & Evidence