Chimyl alcohol labelled

The autoradiograph in Fig. 96 shows the analysis of the intermediate products formed in a synthesis of several stages. Radioactively labelled chimyl alcohol was prepared in accordance with, the following scheme... 

Fig. 96. Application of TLC in the control of the synthesis of radioactively labelled chimyl alcohol (a-hexadecyl glycerol ether) from palmitic acid-1[425]. (see reaction scheme above) Layer silica gel G solvent petrol ether (BP 60—70° C)-diethyl ether-acetic acid (80 - - 20 + 1) time of run 1 h autoradiograph. 1 palmitic acid 2 methyl palmitate 3 crude pahnityl alcohol 4 recrystallised palmityl alcohol 5 filtrate from (3) 6 crude palmityl mesylate 7 recrystallised palmityl mesylate 8 filtrate from 6) 9 crude acetone ketal of chimyl alcohol 10 crude chimyl alcohol 11 recrystallised chimyl alcohol 12 filtrate from 10)...

We have also prepared doubly labeled a-chimyl alcohol from hexa-decyl-l-C -bromide and isopropylidene-2-H -glycerol in the manner described for batyl alcohol. P-Glyceryl ethers were synthesized by Oswald et al. (1966) from the potassium salt of 1,3-benzylidene glycerol and the alkyl bromide. DL-P-l-C -Chimyl alcohol was obtained in 40% yield with a radiopurity of 99-100% and a specific activity of 1 mCi/mmole. 

Figure 24.4. Synthesis of enantiomerically pure, positionally labeled, structured ether lipids of the ALM type by chemoenzymatic approach, starting from enantiomerically pure chimyl (S-4), batyl (S-5) and selachyl (S-6) alcohols.

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