(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-hydroxy-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate -Drug Synthesis Database

【结构式】

【分子编号】62178

【品名】(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-hydroxy-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate

【CA登记号】

【分子式】C₂₈H₄₃NO₇

【分子量】505.65196

【元素组成】C 66.51% H 8.57% N 2.77% O 22.15%

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：(XLII)

Treatment of diester (XLI) with LiOH produces a mixture of hydrolyzed products, from which the desired mono-acetylated compound (XLII) can be separated from its mono-acetyl regiosiomer and the fully hydrolyzed product. Epoxidation of the exocyclic olefin (XLII) with m-CPBA furnishes diastereoselectively epoxide (XLIII). Finally, deacetylation of the methyl ketal (XLIII) to the target hemiketal compound is achieved by treatment with an acidic cation-exchange resin in wet THF.

参考文献中间体

合成目标

【1】 Horigome, M.; Motoyoshi, H.; Watanabe, H.; Kitahara, T.; A synthesis of FR901464. Tetrahedron Lett 2001, 42, 46, 8207.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XLI)	62177	(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-(acetyloxy)-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate	C₃₀H₄₅NO₈	详情	详情
(XLII)	62178	(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(2R,3S,6S)-3-hydroxy-6-methoxy-6-methyl-4-methylenetetrahydro-2H-pyran-2-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate	C₂₈H₄₃NO₇	详情	详情
(XLIII)	62179	(1S,2Z)-4-[((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-methoxy-7-methyl-1,6-dioxaspiro[2.5]oct-5-yl]-3-methyl-2,4-pentadienyl}-2,5-dimethyltetrahydro-2H-pyran-3-yl)amino]-1-methyl-4-oxo-2-butenyl acetate	C₂₈H₄₃NO₈	详情	详情

Extended Information