2-O-Methyl- and 3,6-Di-O-methyl-cellulose from Natural Cellulose: Synthesis and Structure Characterization

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• 作者：Atsushi Nakagawa ; Chiyo Ishizu ; Velina Sarbova ; Andreas Koschella ; Toshiyuki Takano ; Thomas Heinze ; Hiroshi Kamitakahara
• 刊名：Biomacromolecules
• 出版年：2012
• 出版时间：September 10, 2012
• 年：2012
• 卷：13
• 期：9
• 页码：2760-2768
• 全文大小：520K
• 年卷期：v.13,no.9(September 10, 2012)
• ISSN：1526-4602

文摘

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 ¹H and ¹³C NMR spectroscopy of the acetates of 2MC and 36MC. 2MC and 36MC were soluble in water and did not show thermoreversible gelation.