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Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2011 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 7, 1-9 p.Article in journal (Refereed) Published
Abstract [en]

Diglycose derivatives, consisting of two monosaccharides linked at non-anomeric positions by a bridging nitrogen atom, have been synthesised. Conversion of one of the precursor monosaccharide coupling components into an unsaturated derivative enhances its electrophilicity at the allylic position, facilitating coupling reactions. Mitsunobu coupling between nosylamides and 2,3-unsaturated-4-alcohols gave the 4-amino-pseudodisaccharides with inversion of configuration as single regio- and diastereoisomers. A palladium-catalysed coupling between an amine and a 2,3-unsaturated 4-trichloroacetimidate gave a 2-amino-pseudodisaccharide as the major product, along with other minor products. Derivatisation of the C=C double bond in pseudodisaccharides allowed the formation of Man(N4-6)Glc and Man(N4-6)Man diglycosides. The amine-linked diglycosides were found to show weak glycosidase inhibitory activity.

Place, publisher, year, edition, pages
2011. Vol. 7, 1-9 p.
Keyword [en]
amination, glycomimetics, glycosidases, Mitsunobu, pseudodisaccharides
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:su:diva-68311DOI: 10.3762/bjoc.7.128ISI: 000293968600001OAI: oai:DiVA.org:su-68311DiVA: diva2:477424
Note

authorCount :8

Available from: 2012-01-13 Created: 2012-01-03 Last updated: 2017-12-08Bibliographically approved

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