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

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 agains...

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Bibliographic Details
Published in:Reports in organic chemistry 2014-01, Vol.4, p.1
Main Authors: Hasty, Scott J, Ranade, Sneha C, Demchenko, Alexei V
Format: Article
Language:English
Subjects:
Carbohydrates
Chemistry
Chromatography
Glycosylation
NMR
Nuclear magnetic resonance
Physiological aspects
Silver compounds
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Summary: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.
ISSN:2230-5246
2230-5246
DOI:10.2147/ROC.S32147