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The synthesis of a series of short poly(norbornene)s displaying pendant disaccharides is reported. para-(Propargyloxy)benzyl moieties were attached to a norbornenyl group via an ester or amide linkage, giving two different pre-monomers. A set of protected beta-(1?6)-linked glucosamine-based disaccharides, structurally similar to the bacterial biofilm constituent poly-N-acetylglucosamine (PNAG), were attached to the pre-monomers via a Huisgen 1,3-dipolar cycloaddition reaction to generate a series of ‘glycomonomers’. In the presence of a Grubbs’ 3rd generation catalyst, the glycomonomers displayed variable reactivities that were dependent on the type of linkage (ester or amide) between the norbornenyl and benzyl moieties. In general, the amide-linked glycomonomers polymerized at a much slower rate and had a comparatively lower degree of polymerization than the corresponding ester-linked constructs. All the materials displayed a relatively narrow molecular weight distribution ( = 1.2-1.5).
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI