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Journal of Lipid Research, Vol 27, 344-351, Copyright © 1986 by Lipid Research, Inc.

ARTICLES

Convenient synthesis of racemic mixed-chain ether glycerophosphocholines from fatty alkyl allyl ethers: useful analogs for biophysical studies

NM Witzke and R Bittman

Diether glycerophosphocholines containing one long and one short chain were synthesized in moderate yield. The synthesis of a diether glycerophosphocholine containing a branched chain and a straight chain is also described. Alkylation of fatty alcohol with allyl bromide and dimethyl sulfoxide anion gave fatty alkyl allyl ether, which was hydroxylated and tritylated. By procedures described previously, 1-O- alkyl-3-O-triphenyl-methylglycerol was alkylated, detritylated, and converted into the phosphocholine product. This method is of general utility for the preparation of a variety of mixed-chain racemic glycerophosphocholines whose physical properties are of interest in studies of biological membranes.
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