Process for synthesis of 5.alpha.-cholest-8(14)-en-3.beta.-ol-15-one and other 15-oxygenated sterols

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dc.contributor.assigneeRice Universityen_US
dc.contributor.publisherUnited States Patent and Trademark Officeen_US
dc.creatorSchroepfer, George J., Jr.en_US
dc.creatorWilson, William K.en_US
dc.creatorWang, Ker-shien_US
dc.creatorKisic, Alemkaen_US
dc.date.accessioned2015-05-04T19:05:27Z
dc.date.available2015-05-04T19:05:27Z
dc.date.filed1988-02-05en_US
dc.date.issued1990-01-30en_US
dc.description.abstractA process for preparing 15-oxygenated sterols, such as 3β-hydroxy-5α-cholest-8(14)-ene-15 one, comprising converting 7-dehydrocholesterol to 3β-benzoyloxycholesta-5,7-diene, converting the 3β-benzoyloxycholesta-5,7-diene to a 3β-benzoyloxy-5-cholesta-7,14-diene, converting the 3β-benzoyloxy-5-cholesta-7,14-diene to a 3β-benzoyloxy-14α, 15α-epoxy-5-cholest-7-ene and converting the 3β-benzoyloxy-14α, 15α-epoxy-5-cholest-7-ene to a 15-oxygenated sterol. Preferably, the 3β-benzoyloxy-cholesta-5,7-diene is converted to a 3β-benzoyloxy-5-cholesta-7,14-diene by (i) contacting 3β-benzoyloxy-cholesta-5,7-diene, in a solvent at a temperature of at most about -55° C., with HCl at a concentration of at least about 2.0 M for a time sufficient to convert the 3β-benzoyloxycholesta-5,7-diene to a 3β-benzoyloxy-5-cholesta-7,14-diene; (ii) neutralizing the resultant reaction mixture with a base to prevent formation of a significant amount of 3β-benzoyloxy-5-cholesta-8,14-diene; and (iii) recovering the 3β-benzoyloxy-5-cholesta-7,14-diene.en_US
dc.digitization.specificationsThis patent information was downloaded from the US Patent and Trademark website (http://www.uspto.gov/) as image-PDFs. The PDFs were OCRed for access purposes.en_US
dc.format.extent14 ppen_US
dc.identifier.citationSchroepfer, George J., Jr., Wilson, William K., Wang, Ker-shi and Kisic, Alemka, "Process for synthesis of 5.alpha.-cholest-8(14)-en-3.beta.-ol-15-one and other 15-oxygenated sterols." Patent US4897475A. issued 1990-01-30. Retrieved from https://hdl.handle.net/1911/79819.
dc.identifier.patentIDUS4897475Aen_US
dc.identifier.urihttps://hdl.handle.net/1911/79819
dc.language.isoengen_US
dc.titleProcess for synthesis of 5.alpha.-cholest-8(14)-en-3.beta.-ol-15-one and other 15-oxygenated sterolsen_US
dc.typeUtility patenten_US
dc.type.dcmiTexten_US
dc.type.genrepatentsen_US
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