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Hot Topics in Polysaccharide Chemistry – Selected Examples
Author(s) -
Heinze Thomas
Publication year - 2009
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200950603
Subject(s) - cellulose , chemistry , moiety , polysaccharide , nucleophile , alkyne , nucleophilic substitution , ether , organic chemistry , polymer chemistry , combinatorial chemistry , catalysis
Summary: The paper highlights recent developments in polysaccharide chemistry. Cellulose tert‐butyl‐ and thexyldimethylsilyl ethers with degree of substitution up to 2 were accessible and comprehensively characterized by means of NMR spectroscopy. These derivatives enable the preparation of 3‐ O ‐functionalized cellulose ethers. Especially the allyl ether as protecting group at position 3 can be used for the synthesis of 2,6‐di‐ O ‐methyl cellulose. Nucleophilic displacement reactions of cellulose p ‐toluenesulfonic acid esters with amines afforded deoxyamino celluloses that form stable monolayers on different substrates. Based on 6‐deoxy‐6‐azido cellulose, dendrons with a focal alkyne moiety were bound via the copper(I) catalyzed Huisgen reaction. Moreover, dextran derivatives were synthesized that form stable nanoparticles useful, e.g., for the determination of the pH value in biological systems.