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- Title
C-Aryl Glycosylation via Interrupted Pummerer Rearrangement.
- Authors
Jiagen Li; Xuefeng Jiang
- Abstract
C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery, due to their distinctive attributes of resistance to hydrolysis from enzymes. Herein, C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process, featured with sulfonium-tethered [3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols. This protocol offers a broad substrate scope with diverse glycosyl and phenols. Dapagliflozin, Empagliflozin, and Ipragliflozin analogs were straightforward achieved, respectively.
- Subjects
DRUG discovery; GLYCOSYLATION; DRUG derivatives; GLYCALS; IPRAGLIFLOZIN
- Publication
Chinese Journal of Chemistry, 2023, Vol 41, Issue 21, p2843
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202300308