82178-69-6Relevant academic research and scientific papers
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
Broek, A. D:,Lugtenburg, J.
, p. 102 - 105 (2007/10/02)
10-Mono-, 11-mono- and 10,11-dideuterioretinal (in the all-trans, 9-cis, 11-cis and 13-cis forms) of > 98 percent purity and the required (> 96 percent) deuterium incorporation were prepared via LiAlH4 or LiAlD4 reduction of the retinylidene derivative 8.Compound 8 was prepared 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 and commercial 4,4-dimethoxy-2-butanone (4).Exchange of 4 with D2O and base gave 4,4-dimethoxy-1,1,1,3,3-pentadeuterio-2-butanone (4a), which in turn, using the same synthetic method, finally provided 14,20,20,20-tetradeuterioretinal.
