An efficient three‐step strategy for the convenient synthesis of Sn‐glycero‐3‐phosphoethanolamine (GroPEtn) from a commercially available 1,2‐dipalmitoyl‐sn‐glycero‐3‐phosphoethanolamine (DPPE) is reported. Direct hydrolysis of DPPE produces a complex inseparable mixture, hence a protection and deprotection strategy is employed to prepare GroPEtn. The primary amine of DPPE is protected with a highly stable acid‐labile trityl group, followed by strong base hydrolysis of N‐trityl‐DPPE gives N‐trityl‐GroPEtn. Further a mild, rapid, and efficient deprotection method is established using trifluoroacetic acid to remove N‐trityl moiety, affords GroPEtn as a single product. This is the first semisynthetic approach and efficient method to produce GroPEtn with a total yield of 66% in three steps. GroPEtn did not show any cytotoxicity against human kidney (HK‐2) cells and reporter gene assay for activation of Keap1‐Nrf2‐mediated antioxidant defense mechanism showed no significant effects.

中文翻译：

---

一种简单高效的合成sn-甘油-磷酸乙醇胺的方法。

据报道，一种有效的三步策略可方便地从市售的1,2-二棕榈酰-sn-甘油-3-磷酸乙醇胺（DPPE）合成Sn-甘油-3-磷酸乙醇胺（GroPEtn）。DPPE的直接水解会产生复杂的不可分离的混合物，因此采用保护和脱保护策略来制备GroPEtn。DPPE的伯胺与高度稳定的酸不稳定基三苯甲基，随后的强碱水解受保护的N-三苯甲基DPPE给出Ñ三苯甲基GroPEtn。此外，建立了使用三氟乙酸去除N的温和，快速，有效的脱保护方法-三苯甲基部分，可将GroPEtn作为单一产品提供。这是在三个步骤中以66％的总收率生产GroPEtn的第一种半合成方法和有效方法。GroPEtn没有显示出对人肾（HK-2）细胞的任何细胞毒性，并且针对Keap1-Nrf2介导的抗氧化剂防御机制的激活基因的报告基因检测未见明显影响。