Synthesis of 1, 2-di-O-alkyl-sn-glycero-3-phosphatidylcholine using 2-methoxyethoxymethyl and 2-(trimethylsilyl) ethoxymethyl protective groups.

K Yamauchi, M Hihara, M Kinoshita

Index: Yamauchi, Kiyoshi; Hihara, Mitsuyoshi; Kinoshita, Masayoshi Bulletin of the Chemical Society of Japan, 1987 , vol. 60, p. 2169 - 2172

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Citation Number: 9

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 ...