Preparation of deuterium-labelled retinals having high deuterium content on specific positions 10-Mono-, 11-mono-, 10,11-di- and 14,20,20,20-tetradeuterioretinal
作者： A. D. Broek , J. Lugtenburg
关键词: Medicinal chemistry 、 Chemistry 、 Crystallography 、 Yield (chemistry) 、 Bromide 、 Deuterium 、 Deuterium labelled 、 Base (chemistry) 、 Turn (biochemistry) 、 Derivative (chemistry)
摘要: 10-Mono-, 11-mono- and 10,11-dideuterioretinal (in the all-trans, 9-cis, 11-cis 13-cis forms) of > 98% purity required (> 96%) deuterium incorporation were prepared via LiAlH4 or LiAlD4 reduction retinylidene derivative 8. Compound 8 was by coupling β-ionone with 6,6-dimethoxy-4-methyl-3-hexen-1-yne (6), which had been obtained in high yield from 2-propynyl bromide commercial 4,4-dimethoxy-2-butanone (4). Exchange 4 D2O base gave 4,4-dimethoxy-1,1,1,3,3-pentadeuterio-2-butanone (4a), turn, using same synthetic method, finally provided 14,20,20,20-tetradeuterioretinal.
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