What question did this study set out to answer?

To develop a high-yield, streamlined multi-step synthetic pathway for preparing deuterium-labeled methyl cis-9-octadecenoate.

October 1, 1978Journal of Labelled Compounds and Radiopharmaceuticals

Synthesis of methyl cis-9-octadecenoate-14, 14, 15, 15, 17, 18-d6

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Authors

RAR. O. AdlofNorthern Illinois University EEE. A. EmkenNorthern Illinois University

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Implication

Experimental study demonstrates efficient synthesis of deuterated methyl octadecenoate in chemical systems, indicating a versatile route for preparing monoenoic fatty acid isomers.

Key Points

To develop a high-yield, streamlined multi-step synthetic pathway for preparing deuterium-labeled methyl cis-9-octadecenoate.
Implemented a six-step synthetic sequence centered on a 2-alkoxytetrahydropyran intermediate.
Converted the intermediate directly to an alkyl iodide in >90% yield.
Coupled the resulting deutero alkyl iodide to an aldehydic ester using the Wittig reaction.
Achieved an overall synthetic yield of 45% to 55%, with every individual reaction step prior to the final Wittig coupling exceeding 90% yield.
Attained deuterium incorporation with isotopic purity exceeding 84%.
Established synthetic versatility for preparing diverse positional monoenoic fatty acid isomers by modulating the chain length of the deutero alkyl iodide.

Cite This Study

Adlof et al. (1978) studied this question.

synapsesocial.com/papers/6a9282ee1bc865c26749fbf1 https://doi.org/10.1002/jlcr.2580150114

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Implication

Experimental study demonstrates efficient synthesis of deuterated methyl octadecenoate in chemical systems, indicating a versatile route for preparing monoenoic fatty acid isomers.

Synthesis of methyl cis-9-octadecenoate-14, 14, 15, 15, 17, 18-d6

Discussion

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Implication

Key Points

Cite This Study

Synthesis of methyl cis-9-octadecenoate-14, 14, 15, 15, 17, 18-d6

Discussion

Member takes

Implication

Key Points

Cite This Study

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