allyl 2-methoxy-5-[(3,4,5-trimethoxyphenoxy)methyl]phenyl ether; 5-[[3-(allyloxy)-4-methoxybenzyl]oxy]-1,2,3-trimethoxybenzene -Drug Synthesis Database

【结构式】

【分子编号】48351

【品名】allyl 2-methoxy-5-[(3,4,5-trimethoxyphenoxy)methyl]phenyl ether; 5-[[3-(allyloxy)-4-methoxybenzyl]oxy]-1,2,3-trimethoxybenzene

【CA登记号】

【分子式】C₂₀H₂₄O₆

【分子量】360.40696

【元素组成】C 66.65% H 6.71% O 26.64%

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)

Isovanillin (I) was protected as the allyl ether (III) by treatment with allyl bromide (II) and K2CO3. Aldehyde reduction of (III) with NaBH4 gave alcohol (IV), which was converted to chloride (V) using SOCl2. Condensation of chloride (V) with the sodium salt of 3,4,5-trimethoxyphenol (VI) produced the corresponding ether (VII). Finally, deprotection of the allyl group of (VII) was achieved by treatment with Wilkinson’s catalyst and DABCO.

参考文献中间体

合成目标

【1】 McGown, A.T.; Hadfield, J.A.; Rennison, D.; Woo, M.; Lawrence, N.J.; Antimitotic and cell growth inhibitory properties of combrestastatin A-4-like ethers. Bioorg Med Chem Lett 2001, 11, 1, 51.

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)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情
(III)	48348	3-Allyloxy-4-methoxybenzaldehyde		C₁₁H₁₂O₃	详情	详情
(IV)	48349	[3-(allyloxy)-4-methoxyphenyl]methanol		C₁₁H₁₄O₃	详情	详情
(V)	48350	allyl 5-(chloromethyl)-2-methoxyphenyl ether; 2-(allyloxy)-4-(chloromethyl)-1-methoxybenzene		C₁₁H₁₃ClO₂	详情	详情
(VI)	37163	3,4,5-trimethoxyphenol		C₉H₁₂O₄	详情	详情
(VII)	48351	allyl 2-methoxy-5-[(3,4,5-trimethoxyphenoxy)methyl]phenyl ether; 5-[[3-(allyloxy)-4-methoxybenzyl]oxy]-1,2,3-trimethoxybenzene		C₂₀H₂₄O₆	详情	详情

Extended Information