Mwakwari Sandra C, Bess Laura S, Bazin Hélène G, Johnson David A
GSK Vaccines, 553 Old Corvallis Road, Hamilton, MT 59840, USA.
Tetrahedron Lett. 2016 May 11;57(19):2093-2096. doi: 10.1016/j.tetlet.2016.03.110. Epub 2016 Apr 1.
The chemical synthesis of lysophospholipids often involves multiple synthetic and chromatographic steps due to the incorporation of the fatty acyl group onto the glycerol scaffold early in the synthesis. We report herein a new protocol for the lysophosphatidylation of alcohols and its application to the synthesis of lysophospholipid conjugates of TLR7/8-active imidazoquinoline . This new procedure, which is based on the tin-mediated regioselective acylation of late-stage phosphoglycerol intermediate , overcomes many of the drawbacks of conventional lysophosphatidylation methods and allows introduction of different fatty acyl groups in the penultimate step.
由于在合成早期将脂肪酰基引入甘油骨架，溶血磷脂的化学合成通常涉及多个合成和色谱步骤。我们在此报告一种用于醇的溶血磷脂酰化的新方案及其在合成TLR7/8活性咪唑喹啉的溶血磷脂缀合物中的应用。这种基于锡介导的后期磷酸甘油中间体区域选择性酰化的新方法克服了传统溶血磷脂酰化方法的许多缺点，并允许在倒数第二步引入不同的脂肪酰基。
