(8R,9S,13S,14S,17S)-17-[(2-bromoacetyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate -Drug Synthesis Database

【结构式】

【分子编号】34212

【品名】(8R,9S,13S,14S,17S)-17-[(2-bromoacetyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate

【CA登记号】

【分子式】C₂₇H₂₉BrO₄

【分子量】497.42886

【元素组成】C 65.19% H 5.88% Br 16.06% O 12.87%

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：(V)

The benzoylation of 1,3,5(10)-estratrien-3,17beta-diol (I) with benzoyl chloride (II) by means of NaOH in THF-water gives 3-benzoyloxy-1,3,5(10)-estratrien-17beta-ol (III), which is acylated with bromoacetyl bromide (IV) by means of pyridine in THF-CCl4 yielding 3-benzoyloxy-17beta-bromoacetoxy 1,3,5(10)-estratriene (V). Finally, this compound is condensed with silver 4-[4-[bis(2-chloroethyl)amino]phenyl]butyrate (VI) in DMSO.

参考文献中间体

合成目标

【1】 Asano, K.; Tamura, H.; Tanaka, H.; Enomoto, S.; Novel estradiol compound, its preparation and anti-tumor agent containing the same. BE 0878186; JP 55027121 .
【2】 Castaner, J.; Serradell, M.N.; KM-2210. Drugs Fut 1984, 9, 5, 334.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	34210	(8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol	50-28-2	C₁₈H₂₄O₂	详情	详情
(II)	10643	(1S,2S,3R,4S,7S,8S,10R,13S)-10-(acetoxy)-1,7-bis(benzyloxy)-13-[[tert-butyl(dimethyl)silyl]oxy]-8,12,15,15-tetramethyl-5,9-dioxo-4-[(phenylsulfanyl)methyl]tricyclo[9.3.1.0(3,8)]pentadec-11-en-2-yl benzoate		C₅₅H₆₆O₉SSi	详情	详情
(III)	34211	(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate		C₂₅H₂₈O₃	详情	详情
(IV)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(V)	34212	(8R,9S,13S,14S,17S)-17-[(2-bromoacetyl)oxy]-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl benzoate		C₂₇H₂₉BrO₄	详情	详情
(VI)	34213	silver(1+) 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate		C₁₄H₁₈AgCl₂NO₂	详情	详情

Extended Information