Synthesis of diblock methylcellulose derivatives with regioselective functionalization patterns |
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| Authors: | Atsushi Nakagawa Dominik Fenn Andreas Koschella Thomas Heinze Hiroshi Kamitakahara |
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| Affiliation: | 1. Graduate School of Agriculture, Kyoto University, Kitashirakawa‐Oiwake‐cho, Sakyo‐ku, Kyoto 606‐8502, Japan;2. Friedrich Schiller University of Jena, Institute for Organic Chemistry and Macromolecular Chemistry, Center of Excellence for Polysaccharide Research, Humboldtstrasse 10, D‐07743 Jena, Germany |
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| Abstract: | This article describes a new synthesis strategy to prepare diblock copolymers as model compounds for industrially produced cellulose ethers exemplified with methylcellulose (MC). To elucidate a key structure for thermoreversible gelation of MC, five regioselectively methylated celluloses 1 – 5 (236, 23, 26, 3, and 6 MC), five corresponding methyl‐β‐D‐glucopyranosyl‐(1→4)‐cellulosides 6 – 10 , and five equiv methyl‐β‐D‐glucopyranosyl‐(1→4)‐β‐D‐glucopyranosyl‐(1→4)‐cellulosides 11 – 15 were synthesized for the first time via combination of the glycosyl trichloroacetimidate method and the acid‐catalyzed methanolysis method. The structure of compounds 1 – 15 was confirmed by means of NMR spectroscopy and MALDI‐TOF MS. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011 |
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| Keywords: | diblock copolymers gelation glycosylation methylcellulose oligomers polysaccharides regioselective functionalization |
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