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【结 构 式】

【分子编号】56680

【品名】10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-1-decanol

【CA登记号】

【 分 子 式 】C23H42O3Si

【 分 子 量 】394.67018

【元素组成】C 70% H 10.73% O 12.16% Si 7.12%

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:(XIII)

In a different strategy, 3-methoxysalicylaldehyde (VII) was protected as the silyl ether (VIII) using t-butyldimethylsilyl chloride and Et3N. Wittig reaction of aldehyde (VIII) with (9-hydroxynonyl)triphenylphosphonium bromide (IX) afforded olefin (X). This was alternatively prepared by addition of Grignard reagent (XI) to the aldehyde (VIII) to give carbinol (XII), which was further subjected to dehydration and acetal hydrolysis under acidic conditions to afford (X). Catalytic hydrogenation of olefin (X) furnished the 10-aryl decanol (XIII). The heptadecenyl side chain of (XVI) was then constructed by Swern oxidation of alcohol (XIII) to the corresponding aldehyde (XIV), followed by Wittig reaction with heptyltriphenylphosphonium bromide (XV). Desilylation of (XVI) with tetrabutylammonium fluoride gave the phenol precursor (VI), which was finally oxidized to the desired quinone by the same method as above.

1 Wu, S.J.; Yang, Q.Z.; Chemical studies of Iris pallasii Fisch. var. chinensis Fisch.. Acta Chim Sin 1980, 38, 2, 156.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 56674 2-[(Z)-10-heptadecenyl]-6-methoxyphenol C24H40O2 详情 详情
(VII) 12620 o-Vanillin; 2-Hydroxy-3-methoxybenzaldehyde 148-53-8 C8H8O3 详情 详情
(VIII) 56675 2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxybenzaldehyde C14H22O3Si 详情 详情
(IX) 56676 (9-hydroxynonyl)(triphenyl)phosphonium bromide C27H34BrOP 详情 详情
(X) 56677 (Z)-10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-9-decen-1-ol C23H40O3Si 详情 详情
(XI) 56678 bromo[9-(1-ethoxyethoxy)nonyl]magnesium C13H27BrMgO2 详情 详情
(XII) 56679 1-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-10-(1-ethoxyethoxy)-1-decanol C27H50O5Si 详情 详情
(XIII) 56680 10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)-1-decanol C23H42O3Si 详情 详情
(XIV) 56681 10-(2-{[tert-butyl(dimethyl)silyl]oxy}-3-methoxyphenyl)decanal C23H40O3Si 详情 详情
(XV) 56682 heptyl(triphenyl)phosphonium bromide 13423-48-8 C25H30BrP 详情 详情
(XVI) 56683 tert-butyl{2-[(Z)-10-heptadecenyl]-6-methoxyphenoxy}dimethylsilane; tert-butyl(dimethyl)silyl 2-[(Z)-10-heptadecenyl]-6-methoxyphenyl ether C30H54O2Si 详情 详情
Extended Information