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 inReports in organic chemistry Vol. 4; p. 1
Main Authors Hasty, Scott J, Ranade, Sneha C, Demchenko, Alexei V
Format Journal Article
LanguageEnglish
Published Macclesfield Dove Medical Press Limited 01.01.2014
Taylor & Francis Ltd
Subjects
Carbohydrates
Chemistry
Chromatography
Glycosylation
NMR
Nuclear magnetic resonance
Physiological aspects
Silver compounds
United States
United States > US
Missouri
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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