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【结 构 式】

【分子编号】58467

【品名】(4-{2,6-dimethyl-4-[(triisopropylsilyl)oxy]benzyl}-2-isopropylphenoxy)methyl methyl ether; triisopropyl{4-[3-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}silane

【CA登记号】

【 分 子 式 】C29H46O3Si

【 分 子 量 】470.76794

【元素组成】C 73.99% H 9.85% O 10.2% Si 5.97%

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:(I)

Metalation of the biarylmethane derivative (I) by means of butyllithium, followed by iodination with N-iodosuccinimide, leads to aryl iodide (II). After desilylation of (II) using tetrabutylammonium fluoride, the resultant phenolic compound (III) is alkylated with methyl bromoacetate (IV) to produce ether (V). Palladium-catalyzed coupling between aryl iodide (V) and the phenylethynyl boronate reagent (VI) furnishes the diaryl acetylene (VII). The amino group of (VII) is oxidized to the corresponding nitro derivative employing m-chloroperbenzoic acid, and the methoxymethyl protecting group is then removed by acidic hydrolysis to afford (VIII). Finally, methyl ester hydrolysis in (VIII) in the presence of LiOH gives the target carboxylic acid.

1 Nguyen, N.-H.; et al.; Rational design and synthesis of a novel thyroid hormone antagonist that blocks coactivator recruitment. J Med Chem 2002, 45, 15, 3310.
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) 58467 (4-{2,6-dimethyl-4-[(triisopropylsilyl)oxy]benzyl}-2-isopropylphenoxy)methyl methyl ether; triisopropyl{4-[3-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}silane C29H46O3Si 详情 详情
(II) 58468 (4-{2,6-dimethyl-4-[(triisopropylsilyl)oxy]benzyl}-2-iodo-6-isopropylphenoxy)methyl methyl ether; {4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}(triisopropyl)silane C29H45IO3Si 详情 详情
(III) 58469 4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenol C20H25IO3 详情 详情
(IV) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(V) 58470 methyl 2-{4-[3-iodo-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}acetate C23H29IO5 详情 详情
(VI) 58471   C17H23BKNO 详情 详情
(VII) 58472 methyl 2-{4-[3-[2-(4-aminophenyl)ethynyl]-5-isopropyl-4-(methoxymethoxy)benzyl]-3,5-dimethylphenoxy}acetate C31H35NO5 详情 详情
(VIII) 58473 methyl 2-(4-{4-hydroxy-3-isopropyl-5-[2-(4-nitrophenyl)ethynyl]benzyl}-3,5-dimethylphenoxy)acetate C29H29NO6 详情 详情
Extended Information