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A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2004 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 6, no 26, 4885-4888 p.Article in journal (Refereed) Published
Abstract [en]

A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2004. Vol. 6, no 26, 4885-4888 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-14080DOI: 10.1021/ol048053zOAI: oai:DiVA.org:umu-14080DiVA: diva2:153751
Available from: 2008-04-18 Created: 2008-04-18 Last updated: 2017-12-14Bibliographically approved
In thesis
1. Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
Open this publication in new window or tab >>Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

An efficient and versatile non-destructive method to analyze the progress of solid-phase glycoconjugate synthesis with gel-phase 19F NMR spectroscopy is described. The method relies on use of fluorinated linkers and building blocks carrying fluorinated protective groups. Commercially available fluorinated reagents have been utilized to attach the protective groups.

The influence of resin structures for seven commercial resins upon resolution of gel-phase 19F NMR spectra was investigated. Two different linkers for oligosaccharide synthesis were also developed and successfully employed in preparation of α-Gal trisaccharides and a n-pentenyl glycoside. Finally, reaction conditions for solid-phase peptide glycosylations were established.

Place, publisher, year, edition, pages
Umeå: Kemi, 2005. 82 p.
Keyword
Organic chemistry, Solid-phase synthesis, protective groups, linkers, monitoring, gel-phase, 19F NMR spectroscopy, carbohydrates, oligosaccharides, glycopeptides, Organisk kemi
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-438 (URN)91-7305-792-4 (ISBN)
Public defence
2005-01-21, 13:00
Available from: 2005-01-28 Created: 2005-01-28 Last updated: 2012-06-29Bibliographically approved

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Mogemark, MickaelGustafsson, LindaBengtsson, ChristofferElofsson, MikaelKihlberg, Jan
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