Synthesis of isoxazole conjugates of sugars via 1,3-dipolar cycloaddition

Vaidya, Vipraja V.; Wankhede, Karuna S.; Salunkhe, Manikrao M.; Trivedi, Gaurav

doi:10.1139/v07-145

Cited by 6 publications

(1 citation statement)

References 2 publications

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“…falcarinol has been used as a pesticide. 10 Furthermore, both terminal and internal alkynes have essential role in the synthesis of many organic compounds like; aldehydes, 11 ketones, 12 carboxylic acids, 13 alkenes, 14 triazoles, [15][16][17][18][19] isoxazoles 20,22 and polymer. 23,24 Their conjugated polymers have great conductivity, and they have many applications in organic photonics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose

Al-Asadi,

Mohammed,

Joda

2023

Baghdad Sci.J

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In this work, an important sugar alkynyl ether has been synthesized in two subsequent steps starting from commercially available D-galactose (3). This kind of compounds is highly significant in the synthesis of biologically active molecules such as 1,2,3-triazole and isoxazoles. In the first step, galactose (3) was reacted with acetone in the presence of anhydrous copper (II) sulfate to produce 1,2:3,4-di-O-isopropylidene-α-Dgalactose (4) in good yield. The latter was reacted with excess of 3-bromoprop-1-yne in DMF in the presence of NaOH pellets to afford the target molecule 5 in a very good yield. The temperature of this step is crucial in determining the reaction yield. The exact structure of compound 5 is identified using NMR technique and DFT calculations.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose

Al-Asadi,

Mohammed,

Joda

2023

Baghdad Sci.J

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ChemInform Abstract: Synthesis of Isoxazole Conjugates of Sugars via 1,3‐Dipolar Cycloaddition.

et al. 2008

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Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal‐Free Molecular Clicking

Heaney

2012

Eur J Org Chem

104

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The need for precise and flexible synthetic methodology to underpin modern research in chemical biology and materials science has fuelled a resurgence of interest in Huisgen 1,3‐dipolar cycloaddition chemistry. Of late, the in vogue chemistry for the assembly of complex biological molecules and specialist materials has been the copper‐catalysed azide alkyne cycloaddition (CuAAC) reaction. However, in certain circumstances aversion to the copper catalyst flaws this approach and alternatives have been sought. Click chemistry has developed beyond the original triazole‐forming trick and azides are no longer the only dipoles pursued as click cycloaddition partners. This article reviews some of the complications of the CuAAC reaction and evaluates the potential of nitrile oxide/alkyne cycloaddition (NOAC) as a covalent conjugation tool. With a focus on applications in nucleic acid chemistry and materials science it presents the case for a prominent position for nitrile oxides in the catalyst‐free bioconjugation toolbox.

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Synthesis of isoxazole conjugates of sugars via 1,3-dipolar cycloaddition

Cited by 6 publications

References 2 publications

Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose

Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose

ChemInform Abstract: Synthesis of Isoxazole Conjugates of Sugars via 1,3‐Dipolar Cycloaddition.

Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal‐Free Molecular Clicking

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