162087-52-7

Upstream product

• 162087-49-2 (3E,6Z,9Z)-1-(2-tetrahydropyranyloxy)-dodeca-3,6,9-triene 
• 162087-50-5 (3E,6Z,9Z)-1-bromododeca-3,6,9-triene 
• 130236-41-8 (3E)-1-iodo-6-(2-tetrahydropyranyloxy)-hex-3-ene 
• 130236-43-0 (E)-6-(2-tetrahydropyranyloxy)-hex-3-enyltriphenyl phosphonium iodide 
• 88730-60-3 (E)-6-(tetrahydro-2H-pyran-2-yloxy)hex-3-en-1-ol 
• 104178-62-3 6-<(tetrahydro-2H-pyran-2-yl)oxy>-3-hexyn-1-ol 
• 162087-51-6 (8E,11Z,14Z)-1-(2-tetrahydropyranyloxy)-heptadeca-8,11,14-triene 

Relevant academic research and scientific papers

A divergent synthesis of [1-14C]-mono-E isomers of fatty acids

A convenient synthesis of [1-14C]-mono-trans fatty acid using olefin inversion as a key-step is described. This methodology allows for a facile synthesis of [1-14C]-labelled mono-trans analogues of oleic, linoleic and linolenic acids. As an example, only eleven steps were necessary to obtain the [1-14C]-mono-E isomers of linolenic acid from its commercial all-Z form. In the first step, Barton's decarboxylation procedure yielded a bromo intermediate. Epoxidation of this compound resulted in the formation of three monoepoxides, which could be separated by HPLC. After identification by 1H NMR and MS, the pure monoepoxides were then subjected to inversion consisting of a stereospecific deoxygenation followed by a β-elimination step. Finally, the labelling was introduced by substitution of the bromine by a [14C]-cyano group followed by hydrolysis.

Synthesis of (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids and their -radiolabelled analogs

In order to study the effect of the double bonds geometry of linolenic acid (18:3 n-3) on its biological activities, (9Z,12Z,15E)- and (9E,12Z,15Z)-octadecatrienoic acids, found in many refined vegetable oils, were made by total synthesis. Synthesis of 18