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July 1, 1986Journal of Labelled Compounds and Radiopharmaceuticals

Syntheses of deuterated methyl 9,15‐octadecadienoate and methyl 9,12,15‐octadecatrienoate geometric isomers

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HRHenry RakoffNational Center for Agricultural Utilization Research

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Implication

Experimental study demonstrates the multistep chemical synthesis of deuterated fatty acid ester isomers, highlighting versatile routes for metabolic isotope labeling.

Key Points

To synthesize deuterium-labeled geometric isomers of methyl 9,15-octadecadienoate and methyl 9,12,15-octadecatrienoate using sequential chain-extension and coupling reactions.
Generated intermediate building blocks via cyclohexene ozonolysis, chain extension with phosphonium salts, and catalytic deuteration using deuterium gas with tris(triphenylphosphine)chlororhodium.
Assembled target octadecadienoate and octadecatrienoate skeletons through stereoselective Wittig couplings.
Separated the geometric isomer mixtures generated in each coupling step using silver resin chromatography.
Successfully produced methyl 9,15-octadecadienoate-6,7-d2 isomers by Wittig coupling between methyl 9-oxononanoate-6,7-d2 and 6-nonenyltriphenylphosphonium bromide.
Prepared methyl 9,12,15-octadecatrienoate isomers via chain extension to methyl 12-oxo-9-dodecenoate-6,7-d2 followed by Wittig reaction with 3-hexenyltriphenylphosphonium bromide.
Effectively resolved all resulting geometric isomers produced during the reaction sequences using silver resin chromatography.

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Henry Rakoff (1986) studied this question.

synapsesocial.com/papers/6a99e7dd8548cd35f93fd543 https://doi.org/10.1002/jlcr.2580230704

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Implication

Experimental study demonstrates the multistep chemical synthesis of deuterated fatty acid ester isomers, highlighting versatile routes for metabolic isotope labeling.

Syntheses of deuterated methyl 9,15‐octadecadienoate and methyl 9,12,15‐octadecatrienoate geometric isomers

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Implication

Key Points

Cite This Study

Syntheses of deuterated methyl 9,15‐octadecadienoate and methyl 9,12,15‐octadecatrienoate geometric isomers

Discussion

Member takes

Implication

Key Points

Cite This Study

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