methyl 4,4-dimethoxy-3-oxobutanoate -Drug Synthesis Database

【结构式】

【分子编号】31117

【品名】methyl 4,4-dimethoxy-3-oxobutanoate

【CA登记号】

【分子式】C₇H₁₂O₅

【分子量】176.16928

【元素组成】C 47.73% H 6.87% O 45.41%

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：(IX)

The condensation of genanyl bromide (VIII) with methyl 4,4-dimethoxyacetylacetate (IX) by means of sodium ethoxide in refluxing ethanol gives 1,1-dimethoxy-6,10-dimethyl-5,9-undecadiene-2-one (X), which is submitted to a Wittig condensation with (4-methyl-6-tetrahydropyranyloxy-4-hexenyl)triphenyl phosphonium iodide by means of n-butyllithium in hexane yielding 7-formyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol (XII). Finally, this compound is reduced with NaBH4 in ethanol.

参考文献中间体

合成目标

【1】 Mishima, H.; Ogiso, A.; Kobayashi, S. (Sankyo Co., Ltd.); Polyprenyl piperazines. DE 2717990; FR 2348907; FR 2422617; GB 1534111; JP 52131507; US 4151357 .
【2】 Castaner, J.; Serradell, M.N.; Blancafort, P.; Plaunotol. Drugs Fut 1983, 8, 11, 930.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	31116	(2E)-1-bromo-3,7-dimethyl-2,6-octadiene; trans-Geranyl bromide; Geranyl bromide	6138-90-5	C₁₀H₁₇Br	详情	详情
(IX)	31117	methyl 4,4-dimethoxy-3-oxobutanoate		C₇H₁₂O₅	详情	详情
(X)	31118	(5E)-1,1-dimethoxy-6,10-dimethyl-5,9-undecadien-2-one		C₁₅H₂₆O₃	详情	详情
(XI)	31119	[(E)-4-methyl-7-(tetrahydro-2H-pyran-2-yloxy)-4-heptenyl](triphenyl)phosphonium iodide		C₃₁H₃₈IO₂P	详情	详情
(XII)	31120	(5E)-2-[(Z,4E)-6-hydroxy-4-methyl-4-hexenylidene]-6,10-dimethyl-5,9-undecadienal		C₂₀H₃₂O₂	详情	详情

Extended Information