Journal of Organic Chemistry p. 15945 - 15963 (2020)
Update date:2022-08-03
Topics:
Wang, Cheng-Chung
Chang, Chun-Wei
Lin, Mei-Huei
Wu, Chia-Hui
Chiang, Tsun-Yi
The glycosylation reaction, which is key for the studies on glycoscience, is challenging due to its complexity and intrinsic side reactions. Thioglycoside is one of the most widely used glycosyl donors in the synthesis of complex oligosaccharides. However, one of the challenges is its side reactions, which lower its yield and limits its efficiency, thereby requiring considerable effort in the optimization process. Herein, we reported a multifaceted experimental approach that reveals the behaviors of side reactions, such as the intermolecular thioaglycon transformation and N-glycosyl succinimides, via the glycosyl intermediate. Our mechanistic proposal was supported by low temperature NMR studies that can further be mapped by utilizing relative reactivity values. Accordingly, we also presented our findings to suppress the generation of side products in solving this particular problem for achieving high-yield glycosylation reactions.
View Morejiangsu hualin chemical co.,ltd.
Contact:86-25-87787402
Address:jaingsu,china
Ji'nan Orgachem Pharmaceutical Co.,Ltd
Contact:+86-531-82687810
Address:Jinan
website:http://www.hanwayschem.com
Contact:+86-18502787239(whatsapp)
Address:18-1-802, Green Garden, Jianghan District, Wuhan 430023, China
Jining tiansheng chemical co.,ltd.
Contact:+86-537-5158722
Address:ROOM 1011, BLOCK B, CUIDU INTERNATIOAL BUSINESS CENTER, JINING CITY, CHINA
Shenzhen Feiming Science and Technology Co,. Ltd
Contact:+86-755-85232577
Address:#B2309, Fenglin International Center ,Jixiang Road, Longcheng street, LongGang District, Shenzhen city, Guangdong province, China.
Doi:10.1016/S0040-4039(00)01309-5
(2000)Doi:10.1021/ja01605a027
(1956)Doi:10.1021/jo01102a025
(1958)Doi:10.1021/jo01057a040
(1962)Doi:10.1021/acs.joc.5b01014
(2015)Doi:10.1016/0040-4039(81)80069-X
(1981)