Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues
Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues
复制标题
受天然化学连接启发的选择性 S-脱乙酰化：糖基硫醇和药物巯基类似物的实用合成
DOI：
10.1039/c5gc00084j
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发表时间：
2015-01-01
期刊：
影响因子：
9.8
通讯作者：
Wan, Qian
中科院分区：
文献类型：
--
作者：
Shu, Penghua;Zeng, Jing;Wan, Qian
Glycosyl thiols are useful building blocks for the construction of compounds of biological and synthetic importance. Herein, we report a practical synthetic approach toward the efficient synthesis of glycosyl thiols via chemo- and regioselective S-deacetylation inspired by native chemical ligation. This strategy allows the large scale synthesis of glycosyl thiols by simple purification steps without column chromatography. In addition, deacetylation reagents (DTT) could also be recovered and regenerated by a simple process. Thiol containing taxol and artemisinin analogues were successfully prepared based on this methodology. Finally, auranofin, a glucose-based oral drug used to treat rheumatoid arthritis, was synthesized in concise steps and overall high yields.
