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Controlled synthesis of glycopolymers with pendant D-glucosamine residues by living cationic polymerization

✍ Scribed by Kenji Yamada; Masahiko Minoda; Takeaki Miyamoto

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
205 KB
Volume
35
Category
Article
ISSN
0887-624X

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✦ Synopsis

D-Glucosamine-containing glycopolymers with well-controlled structure were synthesized by living cationic polymerization. To this end, D-glucosamine-containing vinyl ether (VE) of the type [CH 2 |CH(OCH 2 CH 2 OR)] was prepared, where R denotes a 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimide-b-D-glucopyranoside, i.e., the hydroxyl and amino groups in D-glucosamine residues are protected by acetyl and phthaloyl groups, respectively. It was found that (1) the efficient living cationic polymerization of VE monomer is achieved by a combination of ethylaluminum dichloride (EtAlCl 2 ) with an adduct of trifluoroacetic acid (TFA) and isobutyl VE (IBVE) [CH 3 CH(OiBu)OCOCF 3 ] (i.e., TFA/EtAlCl 2 initiating system); and (2) the polymerization in toluene at the elevated temperature (0ЊC) is most suitable to proceed the homogeneous polymerization over the whole conversion range. The molecular weight distribution of the resulting polymers was very narrow ( M w / M n Ç 1.1). Quantitative deprotection of the resulting precursor polymers was successfully achieved with hydrazine monohydrate to afford the corresponding water-soluble polymers with pendant D-glucosamine residues.

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Controlled synthesis of amphiphilic bloc
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Amphiphilic block and statistical copolymers of vinyl ethers (VEs) with pendant glucose residues were synthesized by the living cationic polymerization of isobutyl VE (IBVE) and a VE carrying 1,2:5,6-di-O-isopropylidene-D-glucose (IpGlcVE), followed by deprotection. The block copolymer was prepared

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