Synthesis and chemical behaviour of 17α-butyl-3β,17β-dihydroxy-16-oximino-5-androstene

Synthesis and chemical behaviour of 17α-butyl-3β,17β-dihydroxy-16-oximino-5-androstene

Starting from 3 -hydroxy-16-oximino-5-androsten-17-one (1), the recently synthesized 16-oximino-17 -hydroxy-17 -butyl derivative 2 gave by the Beckmann fragmentation reactionwith titanium(III) chloride or p-toluenesulphonyl chloride the corresponding D-seco derivative 3. However, using acetic anhydr...

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Veröffentlicht in:Journal of the Serbian Chemical Society 2001, Vol.66 (1), p.23-26
Hauptverfasser: Stojanovic, Srdjan, Molnár-Gábor, Dora, Medic-Mijacevic, Ljubica, Sakac, Marija, Penov-Gasi, Katarina
Format: Artikel
Sprache:eng
Schlagworte:
17-aza-d-homo derivatives of androstene
beckmann fragmentation
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Zusammenfassung:Starting from 3 -hydroxy-16-oximino-5-androsten-17-one (1), the recently synthesized 16-oximino-17 -hydroxy-17 -butyl derivative 2 gave by the Beckmann fragmentation reactionwith titanium(III) chloride or p-toluenesulphonyl chloride the corresponding D-seco derivative 3. However, using acetic anhydride, in addition to the 3 -acetoxy D-seco derivative 4, the 17-aza D-homo derivative 5 was obtained. The structure of compound 5 was proposed on the basis of NMR-spectroscopy. nema
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC0101023S