Steroselective synthesis of 2-C-acetonyl-2-deoxy-D-galactosides using 1,2-cyclopropaneacetylated sugar as novel glycosyl donor

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DOIResolve DOI: http://doi.org/10.1021/ol902732w
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TypeArticle
Journal titleOrganic Letters
Volume12
Issue3
Pages540543; # of pages: 4
Abstract1,2-Cyclopropaneacetylated sugar is an effective glycosyl donor, which reacted with various glycosyl acceptors including monosaccharides, amino acids and other alcohols in the presence of BF3∙OEt2 or TMSOTf. The glycosylation is stereoselective in favor of β-anomeric products with BF3•OEt2 as catalyst, whereas TMSOTf-catalyzed glycosylation prefers the r-anomeric products. 2-C-Acetonyl-2-deoxy-D-galactosides were obtained in good yields.
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LanguageEnglish
AffiliationNRC Institute for Biological Sciences; National Research Council Canada
Peer reviewedYes
NPARC number17400931
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Record identifier42b31d83-c5c8-442e-8803-d0a0462e800c
Record created2011-03-25
Record modified2016-05-09
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