首页> 中文期刊> 《化学研究与应用》 >TEMPO/NaBr/NaClO体系催化氧化法合成α-D-葡萄糖醛酸

TEMPO/NaBr/NaClO体系催化氧化法合成α-D-葡萄糖醛酸

         

摘要

Synthesis route of α-D-glucuronic acid was investigated by oxidizing α-D-glucose. The synthesis step was as follows: in the first step.C, of α-D-glucose was protected with methyl,then the primary alcohols hydroxyl groups was catalytically oxidized by TEMPO/NaClO/NaBr system to be carboxyl groups. In the third step,methyl α-D-glucuronide was hydrolyzed to obtain α-D-glucu-ronic acid in diluted hydrochloric acid. And the hydrolysis condition was optimized. Methyl α-D-glucuronide was hydrolyzed in diluted hydrochloric acid for 15h,30h,45h,58h,65h,respectively. HPLC analysis showed that methyl α-D-glucuronide was hydrolyzed completely after reaction for 58h with the highest yield of 64. 90%. The fraction of α-D-glucuronic acid separated by HPLC was collected and evaporated. The melting point of purified α-D-glucuxonic acid was 164. 3 ~ 165. 2℃( m. p. 165 ℃ ) ,and the total yield on the basis of α-D-glucose was 45. 2%.%以α-D-葡萄糖为起始物,用TEMPO/NaBr/NaClO体系催化氧化法合成α-D-葡萄糖醛酸.合成过程为:首先对α-D-葡萄糖上的C1位进行甲基化保护,然后用TEMPO/NaBr/NaClO体系对伯醇羟基进行催化氧化转化为羧基,最后脱甲基.对第三步稀盐酸水解法脱甲基的条件作了优化,分别水解15h、30h、45h、58h、65h,高效液相色谱(HPLC)结果显示,在水解58h时甲基葡萄糖醛酸钠基本水解完毕,葡萄糖醛酸水解得率最高,水解得率为64.9%.经过高效液相色谱提纯后的葡萄糖醛酸熔点为164.3~165.2℃(m.p.165℃),得率(基于α-D-葡萄糖)为45.2%.

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