Published July 22, 2020 | Version v1
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Data from: Cu-Al mixed oxide-catalysed multicomponent synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives

  • 1. Universidad Autónoma Metropolitana
  • 2. Monterrey Institute of Technology and Higher Education

Description

A series of carbohydrate linked-1,2,3-triazole derivatives were synthetized in good yields from glucofuranose and allofuranose diacetonides using as key step a three-component 1,3-dipolar azide-alkyne cycloaddition catalyzed by a Cu-Al mixed oxide. In this multicomponent reaction, Cu-Al mixed oxide/sodium ascorbate system serves as highly reactive, recyclable and efficient heterogeneous catalyst for regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles. The reported protocol has significant advantages over classical CuI/DIPEA or CuSO4/sodium ascorbate conditions in terms of efficiency and reduced synthetic complexity. In addition, the selective deprotection of synthesized di-O-isopropylidene derivatives was also carried out leading to the corresponding mono-O-isopropylidene products in moderate yields. Some of the synthesized triazole glycoconjugates were tested for their in vitro antimicrobial activity using the disk diffusion method against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), as well as fungus (Aspergillus niger) and yeast (Candida utilis). The results revealed that these compounds exhibit moderate to good antimicrobial activity mainly against Gram-negative bacteria.

Notes

Raw NMR data (including 1H, 13C, COSY, HSQC and HMBC experiments) for new synthetized compounds. 

Funding provided by: Consejo Nacional de Ciencia y Tecnología
Crossref Funder Registry ID: http://dx.doi.org/10.13039/501100003141
Award Number: 255819

Funding provided by: Consejo Nacional de Ciencia y Tecnología
Crossref Funder Registry ID: http://dx.doi.org/10.13039/501100003141
Award Number: 1014

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Is cited by
10.1098/rsos.200290 (DOI)