A Second-Generation Tandem Ring-Closing Metathesis Cleavable Linker for Solid-Phase Oligosaccharide Synthesis

Autor:	Jeroen D. C. Codée, Herman S. Overkleeft, Ana R. de Jong, Bas Hagen, Anne Geert Volbeda, Hans van den Elst, Gijsbert A. van der Marel
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Solid-phase synthesis Ring-closing metathesis Tandem Chemistry Alkene Phase (matter) Organic Chemistry Physical and Theoretical Chemistry Metathesis Combinatorial chemistry Linker Catalysis
Zdroj:	European Journal of Organic Chemistry. 2013:6644-6655
ISSN:	1434-193X
Popis:	A tandem ring-closing metathesis cleavable linker system for solid-phase oligosaccharide synthesis has been developed. The acid- and base-stable linker can be readily cleaved with Grubbs second-generation catalyst without the use of alkene additives to liberate the assembled oligosaccharides from the solid support. Application of the linker was shown in three solid-phase oligosaccharide synthesis campaigns. Two frame-shifted hyaluronic acid fragments were prepared, and we also report the synthesis of a trimeric β-1,3-glucan fragment, in which, next to the linker, our recently reported 4-azido-2,2-dimethylbutanoyl (AzDMB) protective group was applied.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::066cbcb43e6a0042eecc52d2f746c017 https://doi.org/10.1002/ejoc.201301055 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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