(1S,2S)-1-(3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol -Drug Synthesis Database

【结构式】

【分子编号】26119

【品名】(1S,2S)-1-(3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol

【CA登记号】

【分子式】C₂₄H₃₆O₇Si

【分子量】464.63114

【元素组成】C 62.04% H 7.81% O 24.1% Si 6.04%

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：(VIII)

Isovanillin (I) was protected as the silyl ether (II) and subsequently reduced to the benzyl alcohol (III). After conversion of (III) to bromide (IV), its reaction with triphenylphosphine gave phosphonium bromide (V). The ylide resulting from deprotonation of (V) with n-butyllithium was then condensed with 3,4,5-trimethoxybenzaldehyde (VI) to afford the required E-stilbene (VII) along with the corresponding Z-isomer, which were separated by column chromatography. Asymmetric Sharpless dihydroxylation of (VII) by means of AD mix-alpha provided the (1S,2S)-diol (VIII). Finally, desilylation of (VIII) using tetrabutylammonium fluoride afforded the target phenol.

参考文献中间体

合成目标

【1】 Pettit, G.R.; Singh, S.B.; Boyd, M.R.; Hamel, E.; Pettit, R.K.; Schmidt, J.M.; Hogan, F.; Antineoplastic agents. 291. Isolation and synthesis of combretastatins A-4, A-5, and A-6. J Med Chem 1995, 38, 10, 1666.
【2】 Pettit, G.R.; et al.; Antineoplastic agents. 410. Asymmetric hydroxylation of trans-combretastatin A-4. J Med Chem 1999, 42, 8, 1459.

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)	18455	3-hydroxy-4-methoxybenzaldehyde; Isovanillin	621-59-0	C₈H₈O₃	详情	详情
(II)	26114	3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxybenzaldehyde		C₁₄H₂₂O₃Si	详情	详情
(III)	26115	(3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyphenyl)methanol		C₁₄H₂₄O₃Si	详情	详情
(IV)	26116	4-(bromomethyl)-2-[[tert-butyl(dimethyl)silyl]oxy]phenyl methyl ether; [5-(bromomethyl)-2-methoxyphenoxy](tert-butyl)dimethylsilane		C₁₄H₂₃BrO₂Si	详情	详情
(V)	26117	(3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxybenzyl)(triphenyl)phosphonium bromide		C₃₂H₃₈BrO₂PSi	详情	详情
(VI)	11136	3,4,5-Trimethoxybenzaldehyde	86-81-7	C₁₀H₁₂O₄	详情	详情
(VII)	26118	tert-butyl[2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]dimethylsilane; tert-butyl(dimethyl)silyl 2-methoxy-5-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl ether		C₂₄H₃₄O₅Si	详情	详情
(VIII)	26119	(1S,2S)-1-(3-[[tert-butyl(dimethyl)silyl]oxy]-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-1,2-ethanediol		C₂₄H₃₆O₇Si	详情	详情

Extended Information