(E,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-phenyl-2-butenal -Drug Synthesis Database

【结构式】

【分子编号】54594

【品名】(E,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-phenyl-2-butenal

【CA登记号】

【分子式】C₁₆H₂₄O₂Si

【分子量】276.45086

【元素组成】C 69.52% H 8.75% O 11.57% Si 10.16%

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：(R)-(VII)

Ethyl (R)-mandelate [(R)-IV] was protected as its tert-butyldimethylsilyl ether and reduced with DIBAL to [(R)-V], which was treated with ethoxycarbonylmethyl-enetriphenylphosphorane, followed by reduction to give [(R)-VI]. Subsequent oxidation to [(R)-VII] and cyclization by reaction with methylhydrazine afforded a mixture of pyrazolines [(R)-VIII]. Oxidation to pyrazole and deprotection yielded [(R)-(+)-I].

参考文献中间体

合成目标

【1】 Farré, A.J.; Frigola, J.; Cizolirtine Citrate. Drugs Fut 2002, 27, 8, 721.
【2】 Hueso, J.; Frigola, J.; Farré, A.; Berrocal, J.; Gutierrez, B.; Preparation of the enantiomers of the analgesic E-3710. Bioorg Med Chem Lett 1993, 3, 2, 269.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(R)-(+)-(I)	54587	(R)-(1-methyl-1H-pyrazol-5-yl)(phenyl)methanol	C₁₁H₁₂N₂O	详情	详情
(R)-(IV)	54591	ethyl (2R)-2-hydroxy-2-phenylethanoate	C₁₀H₁₂O₃	详情	详情
(R)-(V)	54592	(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethanal	C₁₄H₂₂O₂Si	详情	详情
(R)-(VI)	54593	(E,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-phenyl-2-buten-1-ol	C₁₆H₂₆O₂Si	详情	详情
(R)-(VII)	54594	(E,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-4-phenyl-2-butenal	C₁₆H₂₄O₂Si	详情	详情
(R)-(VIII)	54595	tert-butyl(dimethyl)silyl (R)-(1-methyl-4,5-dihydro-1H-pyrazol-5-yl)(phenyl)methyl ether; 5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-1-methyl-4,5-dihydro-1H-pyrazole	C₁₇H₂₈N₂OSi	详情	详情

Extended Information