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
✍ Scribed by A. D. Broek; J. Lugtenburg
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 399 KB
- Volume
- 101
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
10‐Mono‐, 11‐mono‐ and 10,11‐dideuterioretinal (in the all‐trans, 9‐cis, 11‐cis and 13‐cis forms) of > 98% purity and the required (> 96%) deuterium incorporation were prepared via LiAlH~4~ or LiAlD~4~ 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 D~2~O 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.