Syntheses of tetra- and hexadeuterated octadecenoates.
A study of the metabolism in man of cis and trans monoenoic acids required the synthesis of tetra- and hexadeutero-9-octadecenoates. Preparation of methyl 9-octadecenoate-8,8,11,11-d4 (90 mol % deuterium) by the Wittig reaction was accompanied by deuterium scattering with sodium methoxide as the base but not with alkylithium. Scattering occurred in both the aldehyde and phosphorane moieties only when the aldehyde contained deuterium on the alpha carbon. Methyl 9-octadecenoate-8,8,13,13,14-14-d6 (98 mol % deuterium) was also prepared by the Wittig reaction. The deuterated octadecenoates were formed principally as cis isomers. The trans isomers were produced by nitrogen oxide isomerization and separation on a silver ion column.
D003903:Deuterium; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D007553:Isotope Labeling
D005231:Fatty Acids, Unsaturated; D003903:Deuterium