(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13,16,17-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-11-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】33935

【品名】(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13,16,17-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-11-yl acetate

【CA登记号】

【分子式】C₂₅H₄₀O₄

【分子量】404.5902

【元素组成】C 74.22% H 9.97% O 15.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IIa)

The methylation of 11-acetoxy-3-tetrahydropyranyloxy-16alpha,17-alpha-dimethyl-5alpha-pregnane-20-one (Ia) with lithium diisopropylamide and methyl iodide in THF gives 11beta-acetoxy-3beta-hydroxy-16alpha,17alpha,21-trimethyl-5alpha-pregnane-20-one (IIa), which is oxidized with chromic acid in acetone yielding 11beta-acetoxy-16alpha,17alpha,21-trimethylpregnane-3,20-dione (IIIa). This compound is dehydrogenated with dichlorodicyanobenzoquinone (A) in refluxing toluene affording 11beta-acetoxy-16alpha,17alpha,21-trimethyl-DELTA1,4-pregnadiene-3,20-dione (IVa), which is finally hydrolyzed with KOH in methanol. This sequence can also be perfomed with the 11beta-propoxy, 11beta-isobutyroxy derivatives of (Ib-c, IIb-c, IIIb-c and IVb-c).

参考文献中间体

合成目标

【1】 Woods, G.F.; et al.; Alkylated 3,20-diketo-steroids of the pregnane series. DE 2301317; FR 2168006; GB 1416427; JP 50004060; US 3862194 .
【2】 Hillier, K.; Castaner, J.; Trimexolone. Drugs Fut 1977, 2, 10, 695.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	21890	2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile	84-58-2	C₈Cl₂N₂O₂	详情	详情
(Ia)	33932	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexadecahydro-1H-cyclopenta[a]phenanthren-11-yl acetate		C₃₁H₅₀O₅	详情	详情
(Ib)	33933	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexadecahydro-1H-cyclopenta[a]phenanthren-11-yl propionate		C₃₂H₅₂O₅	详情	详情
(Ic)	33934	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexadecahydro-1H-cyclopenta[a]phenanthren-11-yl 2-methylpropanoate		C₃₃H₅₄O₅	详情	详情
(IIa)	33935	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13,16,17-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-11-yl acetate		C₂₅H₄₀O₄	详情	详情
(IIb)	33936	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13,16,17-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-11-yl propionate		C₂₆H₄₂O₄	详情	详情
(IIc)	33937	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-3-hydroxy-10,13,16,17-tetramethylhexadecahydro-1H-cyclopenta[a]phenanthren-11-yl 2-methylpropanoate		C₂₇H₄₄O₄	详情	详情
(IIIa)	33938	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-11-yl acetate		C₂₅H₃₈O₄	详情	详情
(IIIb)	33939	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-11-yl propionate		C₂₆H₄₀O₄	详情	详情
(IIIc)	33940	(5S,8S,9S,10S,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-11-yl 2-methylpropanoate		C₂₇H₄₂O₄	详情	详情
(IVa)	33941	(8S,9S,10R,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-11-yl acetate		C₂₅H₃₄O₄	详情	详情
(IVb)	33942	(8S,9S,10R,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-11-yl propionate		C₂₆H₃₆O₄	详情	详情
(IVc)	33943	(8S,9S,10R,11S,13S,14S,16R,17S)-17-acetyl-10,13,16,17-tetramethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-11-yl 2-methylpropanoate		C₂₇H₃₈O₄	详情	详情

Extended Information