Influence of preparation procedure on polymer composition: Synthesis and characterisation of polymethacrylates bearing β-D-glucopyranoside and β-D-galactopyranoside residues

M. Ambrosi, A. S. Batsanov, N. R. Cameron, B. G. Davis, J. A.K. Howard, R. Hunter

Research output: Contribution to journalArticleResearchpeer-review

46 Citations (Scopus)

Abstract

Methacrylate derivatives bearing β-D-glucopyranoside and β-D-galactopyranoside residues are synthesised by glycosylation of 2-hydroxyethyl methacrylate (HEMA) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide, respectively. β-Selectivity in the glycosylation reactions is ensured by neighbouring-group participation of acetyl groups at O-2 in the glycosyl donors. 2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucosyloxy) ethyl methacrylate (AcGlcEMA, 1a) was obtained as a crystalline solid and its crystal structure was determined by single-crystal X-ray diffraction. Deprotected polymers are synthesised in two parallel ways; either polymerisation of the protected monomers and subsequent deacetylation of the resulting polymers, or polymerisation of the previously deprotected monomers. The number- and weight-average relative molecular masses of both the protected and deprotected polymers are determined by size exclusion chromatography (SEC). Absolute molecular masses are obtained using the previously estimated refractive-index increments, dn/dc. It is found that polymerisation of deprotected monomers leads to polymers of well-defined composition, in contrast to the deacetylation of protected polymers.

Original languageEnglish
Pages (from-to)45-52
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume2
Issue number1
Publication statusPublished - 19 Jan 2002
Externally publishedYes

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