C - Chemistry – Metallurgy – 07 – J
Patent
C - Chemistry, Metallurgy
07
J
C07J 21/00 (2006.01) C07J 1/00 (2006.01) C07J 31/00 (2006.01) C07J 41/00 (2006.01)
Patent
CA 2447780
Steroids containing a cyclohexene moiety are efficiently oxidized to the corresponding .alpha., .beta.-unsaturated ketone using copper iodide and t- butyl hydroperoxide. A steroid compound containing the .alpha., .beta.- unsaturated ketone structure is efficiently converted to the corresponding vicinal diol using a hydroborating reagent followed by oxidative workup, e.g., borane followed by sodium perborate. Benzoyl and substituted benzoyls are superior protecting groups for hydroxyl groups present in the compounds.
Des stéroïdes contenant un groupe fonctionnel de cyclohexène sont efficacement oxydés par un cétone .alpha. et .beta. insaturé utilisant l'iodure de cuivre et l'hydroperoxyde de t-butyle. Un composé stéroïde contenant la structure de cétone .alpha. et .beta. insaturé est efficacement transformé en un diol proche correspondant au moins d'un réactif hydroboré, avec un traitement final d'oxydation (p.ex., borane suivi de perborate de sodium). Le benzoyle et les benzoyles substitués constituent les groupes protecteurs supérieurs pour les groupes hydroxyles présents dans les composés.
Burgoyne David L.
Ji Gueijun
Kelleher Eugene W.
Paschalides Nicholas D.
Ramachandran Kishore
Inflazyme Pharmaceuticals Ltd.
Smart & Biggar
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