((E)-6-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-4-hexenyl)(triphenyl)phosphonium iodide -Drug Synthesis Database

【结构式】

【分子编号】31361

【品名】((E)-6-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-4-hexenyl)(triphenyl)phosphonium iodide

【CA登记号】

【分子式】C₃₁H₄₂IOPSi

【分子量】616.637612

【元素组成】C 60.38% H 6.87% I 20.58% O 2.59% P 5.02% Si 4.55%

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：(V)

The alkylation of ethyl 4,4-diethoxyacetoacetate (I) with geranyl bromide (II) gave ketoester (III), which was further decarbethoxylated upon treatment with KOH in refluxing H2O - EtOH yielding (IV). Wittig condensation of the resulting alpha-acetal ketone (IV) with phosphonium salt (V) in the presence of KH and crown ether provided the Z olefin (VI) as the major isomer. Deprotection of the silyl ether of (VI) with tetrabutylammonium fluoride gave alcohol (VII), which was coupled with phthalimide under Mitsunobu conditions to yield (VIII). Hydrolysis of the acetal group of (VIII) with aqueous AcOH gave aldehyde (IX).

参考文献中间体

合成目标

【1】 Masuda, K.; Akiyama, T.; Tago, K.; Arai, M.; Minami, E.; Kogen, H.; A highly stereoselective synthesis of plaunotol and its thiourea derivatives as potent antibacterial agents against Helicobacter pylori. Bioorg Med Chem Lett 1999, 9, 10, 1347.

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)	31358	ethyl 4,4-diethoxy-3-oxobutanoate		C₁₀H₁₈O₅	详情	详情
(II)	31116	(2E)-1-bromo-3,7-dimethyl-2,6-octadiene; trans-Geranyl bromide; Geranyl bromide	6138-90-5	C₁₀H₁₇Br	详情	详情
(III)	31359	ethyl (4E)-2-(2,2-diethoxyacetyl)-5,9-dimethyl-4,8-decadienoate		C₂₀H₃₄O₅	详情	详情
(IV)	31360	(5E)-1,1-diethoxy-6,10-dimethyl-5,9-undecadien-2-one		C₁₇H₃₀O₃	详情	详情
(V)	31361	((E)-6-[[tert-butyl(dimethyl)silyl]oxy]-4-methyl-4-hexenyl)(triphenyl)phosphonium iodide		C₃₁H₄₂IOPSi	详情	详情
(VI)	31365	tert-butyl[[(2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl]oxy]dimethylsilane; tert-butyl(dimethyl)silyl (2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl ether		C₃₀H₅₆O₃Si	详情	详情
(VII)	31362	(2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol		C₂₄H₄₂O₃	详情	详情
(VIII)	31363	2-[(2E,6Z,10E)-7-(diethoxymethyl)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenyl]-1H-isoindole-1,3(2H)-dione		C₃₂H₄₅NO₄	详情	详情
(IX)	31364	(5E)-2-[(Z,4E)-6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-methyl-4-hexenylidene]-6,10-dimethyl-5,9-undecadienal		C₂₈H₃₅NO₃	详情	详情

Extended Information