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项目整合精选>>>Tacalcitol(hydrate), 1,24(R)-Dihydroxyvitamin D3, PRI-2191, TV-02, Apsor, Vellutan, Curatoderm, Bonalfa
Tacalcitol(hydrate), 1,24(R)-Dihydroxyvitamin D3, PRI-2191, TV-02, Apsor, Vellutan, Curatoderm, Bonalfa
他卡西妥 他骨化醇一水物 Chemical Name: (+)-(1alpha,3beta,5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol; (+)-1alpha,24R-Dihydroxyvitamin D3
CAS No. 57333-96-7, 93129-94-3 (monohydrate)
项目整合开发状态: Launched-1993
项目研究机构: Teijin (Originator), Abiogen (Licensee), Esteve (Licensee), Hermal (Licensee), Lipha (Licensee), Merck KGaA (Licensee), Sato Pharmaceutical (Comarketer)
合成路线:The dehydrogenation of 3beta-hydroxycholest-5-en-24-one with dichlorodicyanobenzoquinone in refluxing dioxane,or of cholest-4-ene-3,24-dione (II) with chloranil in refluxing tert-butyl alcohol gives cholesta-1,4,6-triene-3,24-dione (III),which is epoxidized with 30% H2O2 and NaOH in methanol-dioxane-THF yielding 1 alpha,2alpha-epoxycholesta-4,6-diene-3,24-dione (IV).The reduction of (IV) with Li in liquid NH3 affords 1alpha,3beta,24-trihydroxycholest-5-ene (V),which is benzoylated with benzoyl chloride in pyridine and submitted to column chromatography on silica gel to give 1alpha,3beta,24R-tribenzoyloxycholest-5-ene (VI).The dehydrogenation of (VI) with dibromodimethylhydantoin of N-bromosuccinimide yields lalpha,3beta,24R-trihydroxy-cholesta-5,7-diene (VII),which is finally submitted to irradiation with a medium-pressure Hg lamp in ether.
📌 参考资料/链接：
参考文献标题:1alpha,24-Dihydroxycholecalciferol derivs.and pro
文献作者:Takeshita,T.; Hashimoto,Y.; Kawashima,H.; Ishimoto,S.; Ikekawa,N.; Morisaki,M.(Teijin Ltd.)
参考来源:DE 2526981; US 4022891
📄 详细内容
合成路线:The dehydrogenation of 3beta-hydroxycholest-5-en-24-one with dichlorodicyanobenzoquinone in refluxing dioxane,or of cholest-4-ene-3,24-dione (II) with chloranil in refluxing tert-butyl alcohol gives cholesta-1,4,6-triene-3,24-dione (III),which is epoxidized with 30% H2O2 and NaOH in methanol-dioxane-THF yielding 1 alpha,2alpha-epoxycholesta-4,6-diene-3,24-dione (IV).The reduction of (IV) with Li in liquid NH3 affords 1alpha,3beta,24-trihydroxycholest-5-ene (V),which is benzoylated with benzoyl chloride in pyridine and submitted to column chromatography on silica gel to give 1alpha,3beta,24R-tribenzoyloxycholest-5-ene (VI).The dehydrogenation of (VI) with dibromodimethylhydantoin of N-bromosuccinimide yields lalpha,3beta,24R-trihydroxy-cholesta-5,7-diene (VII),which is finally submitted to irradiation with a medium-pressure Hg lamp in ether.
参考文献标题:TV-02
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1988,13(2),133
合成路线:The dehydrogenation of 3beta-hydroxycholest-5-en-24-one with dichlorodicyanobenzoquinone in refluxing dioxane,or of cholest-4-ene-3,24-dione (II) with chloranil in refluxing tert-butyl alcohol gives cholesta-1,4,6-triene-3,24-dione (III),which is epoxidized with 30% H2O2 and NaOH in methanol-dioxane-THF yielding 1 alpha,2alpha-epoxycholesta-4,6-diene-3,24-dione (IV).The reduction of (IV) with Li in liquid NH3 affords 1alpha,3beta,24-trihydroxycholest-5-ene (V),which is benzoylated with benzoyl chloride in pyridine and submitted to column chromatography on silica gel to give 1alpha,3beta,24R-tribenzoyloxycholest-5-ene (VI).The dehydrogenation of (VI) with dibromodimethylhydantoin of N-bromosuccinimide yields lalpha,3beta,24R-trihydroxy-cholesta-5,7-diene (VII),which is finally submitted to irradiation with a medium-pressure Hg lamp in ether.
参考文献标题:Synthesis of active forms of vitamin D.Part IX.S
文献作者:Ikekawa,N.; Koizumi,N.; Morisaki,M.
参考来源:J Chem Soc - Perkins Trans I 1975,1421
产品链接: CAS No. 57333-96-7›› 产品链接: CAS No.93129-94-3››