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A Second‐Generation Tandem Ring‐Closing Metathesis Cleavable Linker for Solid‐Phase Oligosaccharide Synthesis
Author(s) -
de Jong Ana R.,
Volbeda Anne G.,
Hagen Bas,
van den Elst Hans,
Overkleeft Herman S.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301055
Subject(s) - linker , chemistry , solid phase synthesis , tandem , ring closing metathesis , metathesis , oligosaccharide , combinatorial chemistry , salt metathesis reaction , stereochemistry , organic chemistry , biochemistry , peptide , materials science , polymer , computer science , composite material , polymerization , operating system
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.