Synthesis and Characterization of 1- And 2-Monoglyceryl Ethers of Anteiso Fatty Alcohols, and Reinvestigation of Benzylidene Glycerol Synthesis

The branched-chain fatty alcohols D-(+)-12-methyltetradecanol (C15-anteiso alcohol) and D-(+)-14-methylhexadecanol (C17-anteiso alcohol) were prepared by reduction of the methyl esters of the corresponding C15- and C17-anteiso fatty acids isolated from the lipids of Listeria monocytogenes. The 1- and 2-monoglyceryl ethers were prepared from these alcohols, and tested for effects on circulating leukocyte levels. The synthesis and isolation of the intermediate benzylidene glycerols were also reinvestigated. Reaction intermediates and products were purified and characterized by column, thin-layer, and gas–liquid chromatography and by nuclear magnetic resonance spectroscopy.