Regio- and Stereoselective Organocatalyzed Relay Glycosylations To Synthesize 2-Amino-2-deoxy-1,3-dithioglycosides.
Regio- and Stereoselective Organocatalyzed Relay Glycosylations To Synthesize 2-Amino-2-deoxy-1,3-dithioglycosides.
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DOI：
10.1021/acs.orglett.3c00859
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发表时间：
2023-05
期刊：
影响因子：
5.2
通讯作者：
Yongyong Wan;Meimei Zhou;Liming Wang;Kexin Hu;Deyong Liu;Hui Liu;Jiansong Sun;J. Codée;Qingju Zhang
中科院分区：
文献类型：
--
作者：
Yongyong Wan;Meimei Zhou;Liming Wang;Kexin Hu;Deyong Liu;Hui Liu;Jiansong Sun;J. Codée;Qingju Zhang
在此，我们描述了一种新的方法，通过一锅中继糖基化的3-O-乙酰基-2-硝基葡萄糖供体的2-氨基-2-脱氧-二硫代糖苷的区域和立体选择性收敛合成。这种独特的有机催化接力糖基化反应具有良好的位置和立体选择性，良好的产率，温和的反应条件和广泛的底物范围。以3-O-乙酰基-2-硝基葡萄糖醛为供体，采用分步糖基化和一锅糖基化两种方法，有效地得到了带有1，3-二硫键的2-氨基-2-脱氧葡萄糖苷/甘露糖苷。E.大肠杆菌血清群64成功地使用这种新开发的方法合成。
Herein, we describe a novel methodology for the regio- and stereoselective convergent synthesis of 2-amino-2-deoxy-dithioglycosides via one-pot relay glycosylation of 3-O-acetyl-2-nitroglucal donors. This unique organo-catalysis relay glycosylation features excellent site- and stereoselectivity, good to excellent yields, mild reaction conditions, and broad substrate scope. 2-Amino-2-deoxy-glucosides/mannosides bearing 1,3-dithio-linkages were efficiently obtained from 3-O-acetyl-2-nitroglucal donors in both stepwise and one-pot glycosylation protocols. The dithiolated O-antigen of E. coli serogroup 64 was successfully synthesized using this newly developed method.