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【结 构 式】

【分子编号】17327

【品名】(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-1-benzothiophen-2-yl)phenoxy]tetrahydro-2H-pyran-2-carboxylic acid

【CA登记号】

【 分 子 式 】C34H35NO10S

【 分 子 量 】649.71864

【元素组成】C 62.85% H 5.43% N 2.16% O 24.63% S 4.94%

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:(VII)

The two major metabolites of raloxifene, the glucuronide conjugates (VI) and (VIII) are synthesized as follows: The partial silylation of raloxifene (I) with tert-butyldimethylsilyl chloride (TBDMS-Cl) by means of dimethylaminopyridine (DMAP) in THF/DMF gives a mixture of the monosilylated compounds (II) and (III), which are separated by chromatography. Compounds (II) and (III) are independently condensed with methyl 1,2,3,4-tetra-O-acetyl-D-glucuronate (IV) by means of BF3.OEt2 in dichloromethane yielding protected glucuronides (V) and (VII), respectively. Finally, both compounds are deprotected by a treatment first with LiOH in dioxane to hydrolyzed the ester groups, and then with tetrabutylammonium fluoride in THF to eliminate the silyl groups, thus obtaining the desired metabolites (VI) and (VIII), respectively.

1 Glasebrook, A.L.; Frolik, C.A.; Dodge, J.A.; Cho, S.; Phillips, D.L.; Lugar, C.W.; Osborne, J.J.; Synthesis and estrogen receptor binding affinities of the major human metabolites of raloxifene (LY139481). Bioorg Med Chem Lett 1997, 7, 8, 993.
2 Dodge, J.A.; Stocksdale, M.G.; Jones, C.D.; A chemical probe for the estrogen receptor: Synthesis of the H-3 isotopomer of raloxifene. J Label Compd Radiopharm 1995, 36, 1, 43.
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) 17321 [6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-(2-piperidinoethoxy)phenyl]methanone C28H27NO4S 详情 详情
(II) 17322 [6-[[tert-butyl(dimethyl)silyl]oxy]-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone C34H41NO4SSi 详情 详情
(III) 17323 [2-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-6-hydroxy-1-benzothiophen-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone C34H41NO4SSi 详情 详情
(IV) 17324 methyl (2S,3R,4S,5R)-3,4,5,6-tetrakis(acetoxy)tetrahydro-2H-pyran-2-carboxylate 7355-18-2 C15H20O11 详情 详情
(V) 17325 methyl (2S,3R,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[4-(6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-1-benzothiophen-2-yl)phenoxy]tetrahydro-2H-pyran-2-carboxylate C41H43NO13S 详情 详情
(VI) 17326 methyl (2S,3R,4S,5R,6S)-3,4,5-tris(acetoxy)-6-[(2-(4-hydroxyphenyl)-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-1-benzothiophen-6-yl)oxy]tetrahydro-2H-pyran-2-carboxylate C41H43NO13S 详情 详情
(VII) 17327 (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-(6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-1-benzothiophen-2-yl)phenoxy]tetrahydro-2H-pyran-2-carboxylic acid C34H35NO10S 详情 详情
(VIII) 17328 (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-(4-hydroxyphenyl)-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]-1-benzothiophen-6-yl)oxy]tetrahydro-2H-pyran-2-carboxylic acid C34H35NO10S 详情 详情
Extended Information