A. P. Tulloch
May 1, 1985
Citations
0
Influential Citations
4
Citations
Journal
Chemistry and Physics of Lipids
Abstract
Abstract Methyl [7- 2 H 2 ]-, [9- 2 H 2 ]- and [10- 2 H 3 ]decanoates and the corresopnding deuterated decanols have been synthesized. The 7,7-dideuterodecanoate was prepared starting from methyl 7-oxodecanoate. Reduction with sodium borodeuteride to methyl 7-hydroxy-[7- 2 H]decanoate followed by bromination yielded methyl 7-bromo-[7- 2 H]decanoate, further reduction with sodium borodeuteride in hexamethylphosphoramide gave methyl [7- 2 H 2 ]decanoate with only 7% reduction of the ester group. [7- 2 H 2 ]Decanol was also prepared from the bromo ester by lithium aluminum hydride reduction followed by lithium aluminum deuteride-lithium deuteride reduction. Exchange of sodium 10-undecanoate in deuterium oxide gave 10-[2- 2 H 2 ]undecenoic acid without double bond migration. [9- 2 H 2 ]Decanoic acid was obtained by two-stage reduction of the carboxyl to CH 3 and oxidative cleavage of the double bond. [10- 2 H 3 ]Decanol was prepared from 10-hydroxydecanoic acid by protecting the hydroxyl as the methoxyethoxymethoxy ether and reducing the carboxyl to CD 3 , in two stages, with lithium aluminum deuteride; chromic acid oxidation gave [10- 2 H 3 ]decanoic acid. The 7- 2 H 2 - and 9- 2 H 2 -labelled acids and alcohosl were at least 96% dideuterated and [10- 2 H 3 ]acid and alcohol were 97% trideuterated.