D-赤酮酸内酯的合成

Synthesis of D-erythronolactone by oxidation of erythorbic acid with hydrogen peroxide

D-赤酮酸内酯的合成是一个面向大学二年级本科生的探索性手性合成实验。实验以D-异抗坏血酸为手性底物,以水为溶剂,在碱性条件下,通过双氧水氧化,生成D-赤酮酸盐。再经无机酸催化作用下,形成纯手性化合物—D-赤酮酸内酯。其最佳合成条件为D-异抗坏血酸与过氧化氢物质的量比为1∶2,反应温度42℃,反应时间为30min,收率51%。实验结果表明,此工艺流程符合有机化学实验的要求。

Asymmetric synthesis of D-erythronolactone is an exploratory experiment for second year undergraduates. D-erythronolactone was synthesized via oxidation of erythorbic acid using 33. 6% hydrogen peroxide under alkaline condition. The optimum conditions was the mole ratio of erythorbic acid to H_2O_2 is 1 ∶ 2,the reactions were performed at 42℃ for 30 min. The yield of D-erythronolactone could reach 51% under above conditions. The experimental results show that the process is in accordance with the requirements of organic chemistry laboratory teaching.