Synthesis of a 4-Amino-4-deoxy-D-galacturonic Acid Derivative

Vogel, Christian; Gries, Petra

doi:10.1080/07328309408009176

Cited by 20 publications

(5 citation statements)

References 18 publications

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“…The neighboring substituents and groups, as well as the anomeric configuration of the sugar molecule, play a dynamic role in a successful outcome as evident from the example of synthesis of 4-azido galactoside 30 by S N 2 displacement of the mesyl group (which results in inversion of configuration of the corresponding product) from the mesylate of glucoside 29 using NaN 3 in DMF at elevated temperature (Scheme 10). 161 The reaction of sugar epoxides with NaN 3 , using DMF/H 2 O as the solvent system under heating conditions, causes opening of the epoxide ring via nucleophilic attack of azide ions, leading to the formation of diaxial products. This protocol provides another interesting methodology for generation of an azido group on carbohydrates.…”

Section: Azides and Alkyne Substrates: Benefit For Carbohydratesmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Azides and Alkyne Substrates: Benefit For Carbohydratesmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…4- O -Mesyl glucoside 65 , obtained from the respective orthogonally protected glucose derivative, upon reaction with sodium azide in anhydrous DMF at elevated temperature (130 °C) for 32 h gave 86% yield of the desired 4-azido galactoside derivative 66 (Scheme ). Such displacement reaction (NaN 3 as nucleophile) was followed by displacement of the leaving group (mesyl group at the C-4 position) in an SN 2 manner. Therefore, the resultant product 66 was obtained with inversion of configuration.…”

Section: Carbohydrate-based Azides and Alkynes: Beneficial Partners F...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

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“…A cukoraminosavak szintézisénél az aminosavak két jellemző funkciós csoportját kell kialakítani egy szénhidrát molekulán. Ez aminocsoport esetében, mint láthattuk, legtöbbször azidon keresztül történik, 11,12,51,[59][60][61] míg karboxilcsoport esetében egyszerű oxidációkkal (pl.…”

Section: Az Aminocsoport Kialakításának Lehetőségeiunclassified

Új β-cukoraminosavak előállítása és beépítése foldamerekbe

Gőz¹

2019

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Synthesis of a 4-Amino-4-deoxy-D-galacturonic Acid Derivative

Cited by 20 publications

References 18 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

Új β-cukoraminosavak előállítása és beépítése foldamerekbe

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