isopropyl (3S)-3-(1,3-benzodioxol-5-yl)-3-[6-butyl-2-[2-((2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl)-4-methoxybenzoyl]-3-pyridinyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】27591

【品名】isopropyl (3S)-3-(1,3-benzodioxol-5-yl)-3-[6-butyl-2-[2-((2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl)-4-methoxybenzoyl]-3-pyridinyl]propanoate

【CA登记号】

【分子式】C₄₀H₅₅NO₇Si

【分子量】689.96474

【元素组成】C 69.63% H 8.03% N 2.03% O 16.23% Si 4.07%

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：(XLVI)

Alternatively, pyridine ester (XLI) was condensed with the organolithium reagent derived from the silyl-protected intermediate (XXI) to give the corresponding ketone (XLVI). Subsequent desilylation of (XLVI) with HF to (XLVII), followed by base-catalyzed aldol cyclization afforded (XLVIII). Then, the sequence of oxidation to acid (XLIX) with Jones reagent, followed by deoxygenation with SmI2 and basic hydrolysis provided the title diacid.

参考文献中间体

合成目标

【1】 Frey, L.F.; Devine, P.N.; Tschaen, D.M.; Dolling, U.H.; Tillyer, R.D.; Kato, Y. (Banyu Pharmaceutical Co., Ltd.; Merck & Co., Inc.); Stereoselective deoxygenation reaction. EP 0923557; JP 1999514676; WO 9806700 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXI)	27567	4-bromo-3-((2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl)phenyl methyl ether	C₁₇H₂₉BrO₂Si	详情	详情
(XLI)	27586	methyl 3-[(1S)-1-(1,3-benzodioxol-5-yl)-3-isopropoxy-3-oxopropyl]-6-butyl-2-pyridinecarboxylate	C₂₄H₂₉NO₆	详情	详情
(XLVI)	27591	isopropyl (3S)-3-(1,3-benzodioxol-5-yl)-3-[6-butyl-2-[2-((2S)-3-[[tert-butyl(dimethyl)silyl]oxy]-2-methylpropyl)-4-methoxybenzoyl]-3-pyridinyl]propanoate	C₄₀H₅₅NO₇Si	详情	详情
(XLVII)	27592	isopropyl (3S)-3-(1,3-benzodioxol-5-yl)-3-(6-butyl-2-[2-[(2S)-3-hydroxy-2-methylpropyl]-4-methoxybenzoyl]-3-pyridinyl)propanoate	C₃₄H₄₁NO₇	详情	详情
(XLVIII)	27593	isopropyl (5S,6R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-hydroxy-7-[2-[(2S)-3-hydroxy-2-methylpropyl]-4-methoxyphenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate	C₃₄H₄₁NO₇	详情	详情
(XLIX)	27594	(2S)-3-[2-[(5S,6R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-hydroxy-6-(isopropoxycarbonyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]-5-methoxyphenyl]-2-methylpropionic acid	C₃₄H₃₉NO₈	详情	详情

Extended Information