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Title

Unexpected loss of stereoselectivity in glycosylation reactions during the synthesis of chondroitin sulfate oligosaccharides

AuthorsMena-Barragán, Teresa; Paz, José L. de; Nieto, Pedro M.
KeywordsCarbohydrate chemistry
Chondroitin sulfate
Glycosylation
Oligosaccharide synthesis
Stereoselectivity
Issue Date2019
PublisherBeilstein Institut
CitationBeilstein Journal of Organic Chemistry, 15, 137–144 (2019)
AbstractHere, we present an exploratory study on the fluorous-assisted synthesis of chondroitin sulfate (CS) oligosaccharides. Following this approach, a CS tetrasaccharide was prepared. However, in contrast to our previous results, a significant loss of β-selectivity was observed in [2 + 2] glycosylations involving N-trifluoroacetyl-protected D-galactosamine donors and D-glucuronic acid (GlcA) acceptors. These results, together with those obtained from experiments employing model monosaccharide building blocks, highlight the impact of the glycosyl acceptor structure on the stereoselectivity of glycosylation reactions. Our study provides useful data about the substitution pattern of GlcA units for the efficient synthesis of CS oligomers
Publisher version (URL)https://doi.org/10.3762/2Fbjoc.15.14
URIhttp://hdl.handle.net/10261/175670
DOI10.3762/2Fbjoc.15.14
Appears in Collections:(IIQ) Artículos
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