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【结 构 式】

【分子编号】33906

【品名】1-butyl-1-methyl-3-butynyl trimethylsilyl ether; [(1-butyl-1-methyl-3-butynyl)oxy](trimethyl)silane

【CA登记号】

【 分 子 式 】C12H24OSi

【 分 子 量 】212.40746

【元素组成】C 67.86% H 11.39% O 7.53% Si 13.22%

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:(II)

The sililation of 4-methyl-1-octin-4-ol (I) with trimethylsilyl chloride by means of triethylamine in DMF gives the corresponding silyloxy derivative (II), which is treated with diisobutyl aluminum hydride and I2 in toluene - THF yielding 4-methyl-(RS)-4-trimethylsilyloxy-trans-1-octene-1-yl iodide (III). The condensation of (III) with the complex of copper 1-pentynilyde and HMPT (IV) by means of butyllithium in hexane affords the complex salt (V), which, without isolation, is allowed to react with methyl 7-[3-[(RS)-tetrahydropyranyl-2-oxy]-5-oxo-1-cyclopentenyl]-heptanoate (VI) in ethyl ether to give methyl 7-[3-(tetrahydropyranyl-2-oxy)-2-(4-methyl-4-trimethylsilyloxy-trans-1-octene-1-yl)-5-oxo-cyclopentyl]heptanoate (VII). Finally, this compound is hydrolyzed with a mixture acetic acid - water - THF at room temperature.

1 Collins P.W.; et al.; Influence of the position of the side-chain hydroxy group on the biological properties of prostaglandins. Tetrahedron Lett 1975, 48, 4217-20.
2 Pappo, R.; Collins, P.W.; 16-Oxygenated prostanoic acid derivatives. BE 0827127; DE 2513212; FR 2274289; GB 1492426; JP 50135059; US 3965143 .
3 Castaner, J.; Hillier, K.; SC-29333. Drugs Fut 1977, 2, 12, 817.
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) 29066 4-methyl-1-octyn-4-ol C9H16O 详情 详情
(II) 33906 1-butyl-1-methyl-3-butynyl trimethylsilyl ether; [(1-butyl-1-methyl-3-butynyl)oxy](trimethyl)silane C12H24OSi 详情 详情
(III) 33907 [[(E)-1-butyl-4-iodo-1-methyl-3-butenyl]oxy](trimethyl)silane; (E)-1-butyl-4-iodo-1-methyl-3-butenyl trimethylsilyl ether C12H25IOSi 详情 详情
(IV) 29069 1-pentynylcopper C5H7Cu 详情 详情
(V) 33908   C17H32CuLiOSi 详情 详情
(VI) 33909 methyl 7-[(1R,4S)-2-oxo-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]heptanoate C19H32O5 详情 详情
(VII) 33910 methyl 7-[(1R,2S,3R)-2-[(E)-4-methyl-4-[(trimethylsilyl)oxy]-1-octenyl]-5-oxo-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]heptanoate C31H56O6Si 详情 详情
Extended Information