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《Acta Chimica Sinica》 1966-01
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STEROIDS——XLVIII. THE HYDROXYLATION OF Δ~(5,16,20)-PREGNATRIEN-3β,20-DIOL DIACETATE BY POTASSIUM PERMANGANATE

WANG Zi-Wu; HUANG Minlon Institute of Organic Chemistry, Academia Sinica  
1. On treating Δ~(5,16,20)-pregnatrien-3β,20-diol diacetate (V) with potassium permanganate a hydroxylation product was obtained. Its structure has been assumed to be X instead of VI as proposed previously. 2. When the tetrol (VIII) was treated with acetone-perchloric acid, it formed the acetonide XII, but not XIII as reported in the literature. The latter was prepared from another route starting with VI. Based on these results we suspect the correctness of the assumption that 16α, 17α, 21-trihydroxy-20-keto steroids form 16,17-acetonides under the described conditions.
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