کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
10848133 1070654 2005 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
پیش نمایش صفحه اول مقاله
Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3β-ol
چکیده انگلیسی
Many naturally occurring polyhydroxylated sterols and oxysterols exhibit potent biologic activities. This paper describes reagent and position selectivity of epoxidation and reduction of cholesterol derivatives. Cholesterol was reacted with m-chloroperoxybenzoic acid (m-CPBA) to form 5α,6α-epoxycholestan-3β-ol, but in reaction with 30% H2O2, it did not reacted. 1,4,6-Cholestatrien-3-one was obtained from cholesterol and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. 1,4,6-Cholestatrien-3-one was reacted with 30% H2O2 and 5% NaOH in methanol to give 1α,2α-epoxy-4,6-cholestadien-3-one, which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-cholestadien-3β-ol and reduced with Li metal in absolute ethanol to give 2-ethoxy-1,4,6-cholestatrien-3-one. And 1,4,6-cholestatrien-3-one was epoxidized with m-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4-cholestadien-3-one, which was reacted with NaBH4 to synthesize 6α-hydroxy-4-cholesten-3-one and reduced Li metal in absolute ethanol to form 2-ethoxy-1,4,6-cholestatrien-3-one, respectively. 1,4,6-Cholestatrien-3-one was reduced with NaBH4 in absolute ethanol to form 4,6-cholestadien-3β-ol, which was reacted with 30% H2O2 to leave original compound, but was reacted with m-CPBA to give 4β,5β-epoxy-6-cholesten-3β-ol as the major product and 4β,5β-epoxy-6α,7α-epoxycholestan-3β-ol as the minor product.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Steroids - Volume 70, Issue 4, April 2005, Pages 245-250
نویسندگان
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