Synthesis of 1,2-Di-O-alkyl-sn-glycero-3-phosphatidylcholine Using 2-Methoxyethoxymethyl and 2-(Trimethylsilyl)ethoxymethyl Protective Groups

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Abstract
2-Methoxyethoxymethyl (MEM) and 2-(trimethylsilyl)ethoxymethyl (SEM) groups were used to protect the sn-3-OH of optically active glycerols in the synthesis of 1,2-di-O-octadecyl-sn-glycero-3-phosphatidylcholine. Both MEM and SEM protective groups had advantages of a classical benzyl group by virtue of (i) the facile preparation of 1,2-O-isopropylidene-3-O-(2-methoxyethoxymethyl)-sn-glycerol and its sn-3-O-SEM analog as starting materials and (ii) the rapid demasking of the MEM and SEM moieties in lipid precursors, especially by means of titanium tetrachloride.