Visible-light-mediated synthesis of non-anomeric -aryl glycosides a photoactive electron-donor-acceptor complex

A visible-light-mediated glycosylation reaction between glycosyl redox-active esters and disulfides has been reported, through which a series of S -aryl glycosides were obtained in good yields with satisfactory stereoselectivity. The preliminary mechanistic studies revealed that this transformation...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-11, Vol.59 (92), p.13759-13762
Main Authors: Le Zhang, He, Shiyun, Hou, Jinyu, Ye, Meiling, Chen, Jian, Lv, Guanghui, Huang, Tianle, Yang, Zhongzhen, Wu, Yong
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Summary:A visible-light-mediated glycosylation reaction between glycosyl redox-active esters and disulfides has been reported, through which a series of S -aryl glycosides were obtained in good yields with satisfactory stereoselectivity. The preliminary mechanistic studies revealed that this transformation proceeded via an EDA complex. Moreover, the potential application value was demonstrated in the late-stage functionalisation of drug molecules and a gram-scale experiment. A visible-light-mediated glycosylation reaction between glycosyl redox-active esters and disulfides has been reported, through which a series of S -aryl glycosides were obtained in good yields with satisfactory stereoselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc03474g