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Synthesis of cis and trans methyl 8- and 13-octadecenoate-d2 and d4 isomers

✍ Scribed by R. O. Adlof; W. R. Miller; E. A. Emken

Publisher
John Wiley and Sons
Year
1978
Tongue
French
Weight
502 KB
Volume
15
Category
Article
ISSN
0022-2135

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✦ Synopsis

The synthesis of deuterium labelled, maturated, iscsneric fatty acids was required for a series of triplelabelled feeding experiments. The preparation of the cis and trans isamers of methyl 8-octadecenoate-17,18-d2, methyl 8-octadecmoate-13,13,14,14-dq, methyl 13-octadecenoate-17,18-d2 and methyl 13-octadecenoate-17,17,18,18-dq is described. lhe syntheses utilize tris (triphenylphosphine)chlomfiodiun(1) catalyst for the incorporation of deuteriun. Ihe Quble bond is introduced by coupling a deuterated a w l triphmylphosphoniun salt with the appropriate aldehydic ester using the Wittig reaction. Optimization of conditions has increased the overall yields for these syntheses to 6 0 % and the isotopic purity to ,958.

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