Synthesis of glycosyl chlorides and fluorides via a mild chlorination strategy
Soumyadip Dey1, Adrita Nandy1, Shubhi Dwivedi1
1Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502284, Sangareddy, Telangana, India.
Abstract:
A convenient and practical approach for glycosyl chloride synthesis has been developed using benzene-1,3-disulfonyl chloride as a mild and efficient chlorinating reagent. Employing this method, we successfully synthesized a wide range of glycosyl chlorides, including both armed and disarmed mono- and disaccharides. The protocol was further extended to a one-pot synthesis of glycosyl fluorides via in-situ generation of glycosyl chlorides intermediate using AgBF4 as a fluoride source. This versatile synthetic strategy offers straightforward access to a wide range of O- and N-glycosides in good to excellent yields, highlighting its potential for pharmaceutical studies.
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