2-O-Methyl- and 3,6-di-O-methyl-cellulose from natural cellulose: synthesis and structure characterization.

For the first time, 2-O-methyl- (2MC) and 3,6-di-O-methyl-cellulose (36MC) were synthesized via 3-O-allyl- and 3-O-methyl-cellulose, respectively. Position 6 of 3-O-allyl- and 3-O-methyl-cellulose was protected with the 4-methoxytrityl groups. The reaction time and temperature were optimized to achieve a high regioselectivity at C-6 and to prevent the introduction of the 4-methoxytrityl group at C-2 of the polymer. It was found that the substituent at C-3 of 3-O-functionalized celluloses influenced the reactivity of the hydroxyl group at C-6. The structure was characterized by means of (1)H and (13)C NMR spectroscopy of the acetates of 2MC and 36MC. 2MC and 36MC were soluble in water and did not show thermoreversible gelation.

Citation

Atsushi Nakagawa, Chiyo Ishizu, Velina Sarbova, Andreas Koschella, Toshiyuki Takano, Thomas Heinze, Hiroshi Kamitakahara. 2-O-Methyl- and 3,6-di-O-methyl-cellulose from natural cellulose: synthesis and structure characterization. Biomacromolecules. 2012 Sep 10;13(9):2760-8

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PMID: 22817399

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