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

doi:10.1016/S0144-8617(99)00123-X

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

Biobased Ingredients and Materials

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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 language	English
Pages (from-to)	33-43
Journal	Carbohydrate Polymers
Volume	42
Issue number	1
DOIs	https://doi.org/10.1016/S0144-8617(99)00123-X
Publication status	Published - 1 May 2000

Keywords

polymeres

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10.1016/S0144-8617(99)00123-X

http://www.mendeley.com/research/synthesis-reduction-2nitroalkyl-polysaccharide-ethers

1 Article

GMP Compliant Synthesis of Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2
Heeres, A., van der Hoek, S., Antunes, I. F., Attia, K. A., Jacquet, O., Bulthuis, M., Zijlma, R., Boersma, H. H., van Goor, H., Visser, T. J., Heerspink, H. J. L., Elsinga, P. H. & Stevens, J., 8 Nov 2021, In: Journal of Medicinal Chemistry.
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title = "Synthesis and reduction of 2-nitroalkyl polysaccharide ethers",

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.",

keywords = "polymeres, polymeren",

author = "A. Heeres and Spoelma, {F. F.} and {Van Doren}, {H. A.} and Gotlieb, {K. F.} and Kellogg, {R. M.} and Bleeker, {Ido Pieter}",

year = "2000",

month = may,

day = "1",

doi = "10.1016/S0144-8617(99)00123-X",

language = "English",

volume = "42",

pages = "33--43",

journal = "Carbohydrate Polymers",

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publisher = "Elsevier Science",

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TY - JOUR

T1 - Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

AU - Heeres, A.

AU - Spoelma, F. F.

AU - Van Doren, H. A.

AU - Gotlieb, K. F.

AU - Kellogg, R. M.

AU - Bleeker, Ido Pieter

PY - 2000/5/1

Y1 - 2000/5/1

N2 - 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.

AB - 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.

KW - polymeres

KW - polymeren

U2 - 10.1016/S0144-8617(99)00123-X

DO - 10.1016/S0144-8617(99)00123-X

M3 - Article

VL - 42

SP - 33

EP - 43

JO - Carbohydrate Polymers

JF - Carbohydrate Polymers

SN - 0144-8617

IS - 1

ER -

Synthesis and reduction of 2-nitroalkyl polysaccharide ethers

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GMP Compliant Synthesis of Canagliflozin, a Novel PET Tracer for the Sodium−Glucose Cotransporter 2

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