Abstract
Sweet as sugar: Sialyl sulfoxide protected by N-acetyl-5-N,4-O-oxazolidinone was readily prepared, and its coupling to various sugar acceptors was investigated. When the reaction was promoted by Tf(2)O/(Tol)(2)SO, efficient and highly α-selective sialylation yielded α(2,6), α(2,3), and α(2,4) glycosidic linkages between sialic acid and glucose/glacotose.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Furans / chemical synthesis
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Furans / chemistry*
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Galactose / chemical synthesis
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Galactose / chemistry
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Glucose / chemical synthesis
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Glucose / chemistry
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Glycoconjugates / chemical synthesis
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Glycoconjugates / chemistry*
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Glycosylation
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Methylene Chloride / chemistry*
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N-Acetylneuraminic Acid / chemical synthesis
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N-Acetylneuraminic Acid / chemistry*
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Oxazolidinones / chemical synthesis
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Oxazolidinones / chemistry*
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Sulfonamides / chemical synthesis
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Sulfonamides / chemistry*
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Sulfoxides / chemical synthesis
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Sulfoxides / chemistry*
Substances
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Furans
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Glycoconjugates
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Oxazolidinones
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Sulfonamides
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Sulfoxides
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Methylene Chloride
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triflic anhydride
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N-Acetylneuraminic Acid
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Glucose
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Galactose