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- W2168263833 abstract "Die sterisch gehinderte 17-Hydroxygruppe in Pregnanen läßt sich nur in Gegenwart einer 21-Acetoxygruppe mit Pivalinsäureanhydrid/4-(Dimethylamino)pyridin verestern. Nach dieser Methode wird aus 4c über 5c das Corticosteroid 6 synthetisiert. Dagegen kann das 21-Desoxy-17-pivalat 2e nur auf Umwegen aus dem 21-Pivalat 1d über das Umlagerungsprodukt 2b, das Mesylat 2c und das 21-Bromid 2d hergestellt werden. Die weitere Überführung in das 6α-Methylderivat 8 erfolgt über das 6-Methylensteroid 7. 17-Pivalate Derivatives of Pregnane The sterically hindered hydroxy group at C-17 of pregnane derivatives can be esterified by pivalic anhydride/4-(dimethylamino)pyridine only in the presence of an acetoxy group at C-21. Starting from 4c, the synthesis of corticosteroid 6 can be achieved via 5c by application of this method. However, the 21-deoxypivalate 2e can be obtained only by intramolecular transesterification of 1d to yield 2b, followed by mesylation, and reduction of the corresponding bromide 2d. Further transformation of 2e into the 6α-methyl compound 8 proceeds by transfer hydrogenation and isomerization of the intermediate 6-methylene steroid 7." @default.
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- W2168263833 date "1983-04-15" @default.
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- W2168263833 title "17-Pivalate in der Pregnanreihe" @default.
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- W2168263833 doi "https://doi.org/10.1002/jlac.198319830420" @default.
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