L-薄荷基-β-D-葡萄糖苷的合成

摘要

In order to improve the thermal stability of L - menthol, several coupling methods and their related protection and deprotection reactions for L - menthyl β - D - glucoside synthesizing were investigated, the coupling reaction conditions of β - D - glucose pentaacetate with L - menthol were discussed, and the melting point, optical rotation, NMR, MS and TG of the synthesized product were analyzed.The results showed that; 1) it is feasible to synthesize L - menthyl β - D - glucoside from glucose and L - menthol through three-step reaction of acetylation, coupling, and deprotection; 2 ) the synthesized product is the target product; 3 ) the optimized condition of coupling reaction was solvent CH2C12, n ( β - D - glucose pentaacetate) ; n ( L -menthol) ;n( BF3 ? Et2O) =1∶3∶5, reaction temperature 25 ℃ , and reaction time 10 hours, at which the yield reached 40％ ; 4 ) the synthesized product, L - menthyl β - D - glucoside, featured high thermal stability.%为了提高L-薄荷醇的热稳定性,考察了合成L-薄荷基-β-D-葡萄糖苷的几种偶联方法及其相关保护与脱保护反应,探讨了D-葡萄糖五乙酸酯与L-薄荷醇的偶联反应条件,并对合成产物的熔点、比旋光度、NMR、MS和TG进行了分析.结果表明:①以葡萄糖和L-薄荷醇为原料,通过乙酰化、偶联、脱保护三步反应可合成L-薄荷基-β-D-葡萄糖苷;②合成产物为目标产物;③偶联反应的适宜条件:溶剂CH2Cl2,n(D-葡萄糖五乙酸酯)∶n(L-薄荷醇)∶n(BF3·Et2O)=1∶3∶5,反应温度25℃,反应时间10 h,合成产率40%;④合成产物L-薄荷基-β-D-葡萄糖苷的热稳定性高.