Kates M, Hancock A J
Chem Phys Lipids. 1976 Oct;17(2-3 SPEC NO):155-68. doi: 10.1016/0009-3084(76)90059-1.
The chemical synthesis of 3-O-phytanyl-sn-glycero-1-phosphoric acid (monophytanyl ether analogue of lysophosphatidic acid) was effected by condensation of 1-iodo-2-O-benzyl-3-O-phytanyl-sn-glycerol with silver di-p-nitrobenzyl phosphate in anhydrous toluene followed by catalytic hydrogenolysis of the resulting phosphotriester to remove the benzyl and p-nitrobenzyl groups. Synthesis of 3-O-phytanyl-sn-glycero-1-phosphoryl-1'-sn-glycerol (monophytanyl ether analogue of lysophosphatidyl glycerol) was carried out by conversion of the above phosphotriester to the monosilver salt of the suitably blocked lysophosphatidic acid which was condensed with 1-iodo-2-O-t-butyl-3-O-benzyl-sn-glycerol. Removal of the protecting aromatic and t-butyl groups from the resulting blocked triester intermediate gave the desired phytanyl ether analogue of lysophosphatidyl glycerol. Both lyso analogues were isolated as analytically and chromatographically pure potassium salts. Their physical properties and behavior towards acid hydrolysis are described.
3 - O - 植烷基 - sn - 甘油 - 1 - 磷酸（溶血磷脂酸的单植烷基醚类似物）的化学合成是通过在无水甲苯中使1 - 碘 - 2 - O - 苄基 - 3 - O - 植烷基 - sn - 甘油与二 - 对硝基苄基磷酸银缩合，然后对所得的磷酸三酯进行催化氢解以除去苄基和对硝基苄基来实现的。3 - O - 植烷基 - sn - 甘油 - 1 - 磷酰基 - 1'- sn - 甘油（溶血磷脂酰甘油的单植烷基醚类似物）的合成是通过将上述磷酸三酯转化为适当保护的溶血磷脂酸的单银盐来进行的，该单银盐与1 - 碘 - 2 - O - 叔丁基 - 3 - O - 苄基 - sn - 甘油缩合。从所得的受保护的三酯中间体中除去保护芳基和叔丁基，得到所需的溶血磷脂酰甘油的植烷基醚类似物。两种溶血类似物均作为分析和色谱纯的钾盐分离出来。描述了它们的物理性质和对酸水解的行为。
