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Synthesis of non-glycosidically linked selenoether pseudodisaccharides
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2010 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 16, 2127-2129 p.Article in journal (Refereed) Published
Abstract [en]

Non-glycosidically linked disaccharide mimetics with a selenoether functionality linking the two monosaccharide residues have been synthesised. Protected Glc(Se3–3)Glc, Glc(Se3–6)Glc and Glc(Se3–6)Man structures were obtained. Selenium was introduced by displacement of carbohydrate sulfonates with a selenobenzoate anion. Conversion into diselenides by methanolysis of the benzoate and aerial oxidation was followed by reduction of the diselenides to selenolates, and in situ displacement of a second carbohydrate sulfonate in an SN2 reaction to give selenoethers. Glc(Se3–3)Glc and Glc(Se3–6)Glc were also obtained in deprotected form.

Place, publisher, year, edition, pages
Elsevier Ltd , 2010. Vol. 51, no 16, 2127-2129 p.
Keyword [en]
Selenium; Carbohydrates; Coupling; Glycomimetics; Pseudodisaccharides
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-43429DOI: 10.1016/j.tetlet.2010.02.064ISI: 000276751200011OAI: oai:DiVA.org:su-43429DiVA: diva2:356628
Available from: 2010-10-13 Created: 2010-10-13 Last updated: 2017-12-12Bibliographically approved

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