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• W2037694554 endingPage "129" @default.
• W2037694554 startingPage "115" @default.
• W2037694554 abstract "Protected forms of dehydroepiandrosterone, delta 5 cholenic acid, (25R)-26-hydroxycholesterol and diosgenin were converted to the corresponding delta 5,7 dienes by successive treatment with 1,3-dibromo-5,5-dimethylhydantoin (dibromantin), tetrabutylammonium bromide and tetrabutylammonium fluoride. The crude products, which contained the delta 5,7 species contaminated by minor amounts of the delta 5 and delta 4,6 steroids, were purified by silica gel-AgNO3 chromatography to give the following steroids in approximately 99% purity and at least 50% yield: 3 beta-acetoxyandrosta-5,7-dien-17-one, methyl 3 beta-acetoxychola-5,7-dien-24-oate, (25R)-3 beta,26-diacetoxycholesta-5,7-diene and (25R)-3 beta-acetoxyspirosta-5,7-diene. Analogous treatment of acetate derivatives of pregnenolone and stigmasterol gave 3 beta-acetoxypregna-5,7-dien-20-one and 3 beta-acetoxystigmasta-5,7,22-triene in approximately 50% yield but of lower purity. Full 1H and 13C NMR assignments are given for seven delta 5,7 steroid acetates and the corresponding delta 5 starting materials. Coupling constants for rings A, B and C of delta 5,7 steroids are presented and stereochemical assignments have been made for the following 1H NMR signals: the C-11 protons of delta 5,7 steroids, the C-16 protons of sterols and bile acids, the C-22 and C-23 protons of bile acid esters and the C-28 protons of stigmasterol derivatives." @default.
• W2037694554 created "2016-06-24" @default.
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• W2037694554 date "1992-11-01" @default.
• W2037694554 modified "2023-09-26" @default.
• W2037694554 title "Efficient preparation of steroidal 5,7-dienes of high purity" @default.
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• W2037694554 doi "https://doi.org/10.1016/0009-3084(92)90028-n" @default.
• W2037694554 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/1486654" @default.
• W2037694554 hasPublicationYear "1992" @default.
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