77871-13-7Relevant academic research and scientific papers
Synthesis of 11-cis-retinoids by hydrosilylation-protodesilylation of an 11,12-didehydro precursor: Easy access to 11- and 12-mono- and 11,12-dideuteroretinoids
Bergueiro, Julián,Montenegro, Javier,Saá, Carlos,López, Susana
supporting information, p. 14100 - 14107 (2013/01/15)
An expeditious, highly efficient approach to 11-cis-retinoids was achieved by semihydrogenation of a readily available 11-yne precursor through a hydrosilylation-protodesilylation protocol. The complete chemo-, regio-, and syn-stereoselectivity of the method also allowed direct access to 11- and 12-monodeutero-, and 11,12-dideutero-11-cis-retinoids. The analogous trans series was not accessible by this route, and was synthesized by means of Hiyama coupling. Copyright
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.
10-Mono-, 11-mono-, 12-mono and 11,12-dideuteroretinal
Broek, A. D.,Lugtenburg, J.
, p. 363 - 366 (2007/10/02)
The 11-mono and 12-mono- and 11,12-dideuteroretinal (in the all-trans, 9-cis, 11-cis and 13-cis form) with > 98percent chemical purity and > 95percent mono- and dideuterium incorporation were prepared using the same scheme for all three compounds.The all-
