TITLE

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

AUTHOR(S)
Hasty, Scott J.; Ranade, Sneha C.; Demchenko, Alexei V.
PUB. DATE
January 2014
SOURCE
Reports in Organic Chemistry;2014, Vol. 4, p1
SOURCE TYPE
Academic Journal
DOC. TYPE
Article
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 trilate. 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.
ACCESSION #
94751977

 

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