Sodium periodate → 20-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7-diene

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Reaction Steps

To a solution of 20 mg of sodium metaperiodate in 2 ml of tetrahydrofuran was added dropwise an ice-cooled solution of 41 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylthiopregna-5,7-diene in 1 ml of diethyl ether. The resulting mixture was stirred with ice cooling for 30 minutes, then the insoluble matter was filtered off and washed with diethyl ether, and the filtrate and washings were combined, washed in sequence with an aqueous solution of sodium thiosulfate, water, an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride, then dried and concentrated. The residue was purified by silica gel column chromatography to give 29 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-phenylsulfinylpregna-5,7 -diene.

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