Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

A. Heeres, F. F. Spoelma, H. A. Van Doren, K. F. Gotlieb, R. M. Kellogg, Ido Pieter Bleeker

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Abstract

Several 2-nitroalkyl polysaccharide ethers (from pullulan (1), guar (2), agarose (3), inulin (4), cellulose (5), Na-α-polyglucuronate (6) and hydroxyethyl cellulose (7)) were synthesized by reaction with 2-nitro-1-alkenes (2-nitro-1-propene and 2-nitro-1-butene) formed in situ from 2-nitroalkyl acetates. Moderate to high efficiencies are obtained in concentrated aqueous solution/suspension for addition to 1-4 and 7. Analysis of this new class of polysaccharide derivatives with the aid of labeled 2-nitropropyl-2-13C pullulan revealed that the nitrogroup is a mixture of the nitroalkane and nitronic acid tautomers. Grafting of nitroalkenes is observed and, to a lesser extent, additional reactions of the nitro group (formation of carbonyl, oxime and allyl groups) take place. Reduction of 2-nitroalkyl polysaccharide ethers with Na2S2O4or Na2S2O4/NaBH4leads to complex polysaccharide ethers. The products obtained are most likely mixtures of starting material, nitroso compounds, hydroxylamines, hydroxypropyl ethers and sulfamates.
Original languageEnglish
Pages (from-to)33-43
JournalCarbohydrate polymers
Volume42
Issue number1
DOIs
Publication statusPublished - 2000

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Heeres, A., Spoelma, F. F., Van Doren, H. A., Gotlieb, K. F., Kellogg, R. M., & Bleeker, I. P. (2000). Synthesis and reduction of 2-nitroalkyl polysaccharide ethers. Carbohydrate polymers, 42(1), 33-43. https://doi.org/10.1016/S0144-8617(99)00123-X