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A study of silver (I) perchlorate as an effective promoter for chemical glycosylation with thioimidates and thioglycosides

Authors Hasty S, Ranade S, Demchenko A

Received 5 October 2013

Accepted for publication 25 October 2013

Published 20 February 2014 Volume 2014:4 Pages 1—10


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Scott J Hasty, Sneha C Ranade, Alexei V Demchenko

Department of Chemistry and Biochemistry, University of Missouri–St Louis, St Louis, Missouri, USA

Abstract: It has been previously acknowledged that perchlorate salts may be beneficial for the formation of 1,2-cis glycosides. Here, we demonstrate the effectiveness of silver (I) perchlorate as a powerful promoter of glycosyl thioimidate activation. Improved 1,2-cis selectivity was obtained, compared against that obtained with other silver (I) salts, including commonly-used triflate. The use of a combination of silver (I) perchlorate and methyl sulfenyl bromide to activate thioglycosides was also investigated. The cooperative use of these activation protocols was applied to a one-pot, two-step sequential activation, using thioimidate and thioglycoside building blocks.

Keywords: carbohydrates, glycosylation, perchlorate, methodology, promoter

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