5-[4-hydroxy-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoic acid -Drug Synthesis Database

【结构式】

【分子编号】23822

【品名】5-[4-hydroxy-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoic acid

【CA登记号】

【分子式】C₂₀H₃₀O₅

【分子量】350.4552

【元素组成】C 68.55% H 8.63% O 22.83%

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：(IV)

Arylbutanone (I), which was in equilibrium with its hemiacetal cyclic form, was alkylated with isopropyl 5-bromo-2,2-dimethyl-pentanoate (II) in the presence of NaH to afford ether (III). After saponification of the isopropyl and acetate esters of (III) with ethanolic KOH, the resulting ketoacid (IV) was reduced with NaBH4 to yield hydroxyacid (V). Finally, cyclization of (V) using 2,2'-dipyridyl disulfide, triphenylphosphine and silver perchlorate produced the target macrocyclic lactone.

参考文献中间体

合成目标

【1】 Baldazzi, C.; et al.; Medium sized lactones with hyplipidaemic and antio. Bioorg Med Chem 1999, 7, 2, 411.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	23819	4-hydroxy-2,3,6-trimethyl-5-(3-oxobutyl)phenyl acetate	C₁₅H₂₀O₄	详情	详情
(II)	23820	isopropyl 5-bromo-2,2-dimethylpentanoate	C₁₀H₁₉BrO₂	详情	详情
(III)	23821	isopropyl 5-[4-(acetoxy)-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoate	C₂₅H₃₈O₆	详情	详情
(IV)	23822	5-[4-hydroxy-2,3,5-trimethyl-6-(3-oxobutyl)phenoxy]-2,2-dimethylpentanoic acid	C₂₀H₃₀O₅	详情	详情
(V)	23823	5-[4-hydroxy-2-(3-hydroxybutyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid	C₂₀H₃₂O₅	详情	详情

Extended Information