摘要
以2-乙酰氨基葡萄糖为原料制得糖苷供体化合物1-氯-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖,继续与大豆异黄素的7-位羟基经选择性糖苷化、脱乙酰化两步反应合成了7-O-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖大豆异黄素苷。优化后的糖苷反应的最佳条件是:丙酮为反应溶剂,大豆异黄素、氯代糖和K_2CO_3的摩尔比1∶1.5∶1.5,反应温度为55℃,反应时间6 h,目标化合物总产率为64%,该化合物结构经NMR和HRMS确证,且水溶解度达到0.8mg·mL~(-1)。
2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranosyl chloride wasobtained from 2-acetylglucosamine as a glycoside donor and its further selective glycosylation of C-7 hydroxyl groupof daidzein followed by deacetylation afforded 7-O-2-acetylamino-2-deoxy-β-D-glucopyranose-daidzein with the total of yield 64%.After optimization,glycosylation of daidzein was carried out at 55 ℃ in acetone for 6 h with a 1∶1.5∶1.5 molar ratio mixture of daidzein∶glycoside donor∶K_2CO_3.The structure of target compound was confirmed by NMR and HRMS and its solubility in water was 0.8 mg·mL~(-1).
引文
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