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Selectivity of 1-O-Propargyl-d-Mannose Preparations
Authors:Ilona Krabicov  Bohumil Dolenský  Michal &#x;ezanka
Abstract:Thanks to their ability to bind to specific biological receptors, mannosylated structures are examined in biomedical applications. One of the most common ways of linking a functional moiety to a structure is to use an azide-alkyne click reaction. Therefore, it is necessary to prepare and isolate a propargylated mannose derivative of high purity to maintain its bioactivity. Three known preparations of propargyl-α-mannopyranoside were revisited, and products were analysed by NMR spectroscopy. The preparations were shown to yield by-products that have not been described in the literature yet. Our experiments showed that one-step procedures could not provide pure propargyl-α-mannopyranoside, while a three-step procedure yielded the desired compound of high purity.
Keywords:alkylation  furanose  NMR spectroscopy  mannose  propargyl  pyranose
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