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Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals.

Authors :
Liu XL
Mu QQ
Xu L
Cai X
Li CJ
Zheng ZB
Zhang HH
Wang AD
Xu LW
Source :
Organic letters [Org Lett] 2024 Dec 06; Vol. 26 (48), pp. 10248-10252. Date of Electronic Publication: 2024 Nov 22.
Publication Year :
2024

Abstract

Following the satisfactory catalytic performance of cobalt in the C -glycosylation of glycals, further study of cobalt's application values was performed under mild conditions, leading to a range of highly α-stereoselective 2,3-unsaturated O- , S- , and N- glycosides. The synthetic potential of the developed protocol was underscored by the late-stage functionalization of pharmaceutically relevant molecules including the canagliflozin derivative (a potential candidate for treating type 2 diabetes and alleviating pathological aging). Furthermore, control experiments were conducted to elucidate a reasonable mechanism and rule out the pathway involving the configuration conversion between α- and β- anomers.

Details

Language :
English
ISSN :
1523-7052
Volume :
26
Issue :
48
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
39576136
Full Text :
https://doi.org/10.1021/acs.orglett.4c03637