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A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
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2004 (Engelska)Ingår i: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 6, nr 26, s. 4885-4888Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
American Chemical Society (ACS), 2004. Vol. 6, nr 26, s. 4885-4888
Nationell ämneskategori
Kemi
Identifikatorer
URN: urn:nbn:se:umu:diva-14080DOI: 10.1021/ol048053zScopus ID: 2-s2.0-12344323530OAI: oai:DiVA.org:umu-14080DiVA, id: diva2:153751
Tillgänglig från: 2008-04-18 Skapad: 2008-04-18 Senast uppdaterad: 2023-03-24Bibliografiskt granskad
Ingår i avhandling
1. Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
Öppna denna publikation i ny flik eller fönster >>Solid-phase glycoconjugate synthesis: on-resin analysis with gel-phase ¹9F NMR spectroscopy
2005 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Umeå: Kemi, 2005. s. 82
Nyckelord
Organic chemistry, Solid-phase synthesis, protective groups, linkers, monitoring, gel-phase, 19F NMR spectroscopy, carbohydrates, oligosaccharides, glycopeptides, Organisk kemi
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:umu:diva-438 (URN)91-7305-792-4 (ISBN)
Disputation
2005-01-21, 13:00
Tillgänglig från: 2005-01-28 Skapad: 2005-01-28 Senast uppdaterad: 2012-06-29Bibliografiskt granskad

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Bengtsson, ChristofferElofsson, MikaelKihlberg, Jan

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