Synthesis of 1,2,3-Triazole and Tetrazole Appended Glycoconjugates Based on 3,6-Anhydroglucofuranose via Click Reaction

Synthesis of O-glycosyl 1,2,3-triazoles and tetrazole based on the 3,6-anhydro-β-d-glucofuranoside core of natural sauropunols is reported herein. Toward the objective, O-glycosyl alkynes and nitriles, derived from easily available 3,6-anhydro-1,2-O-isopropylidene-5-O-benzoyl-α- d-glucofuranose using three different alcohols under the modified methanolysis procedure, were subjected to a click reaction using organic and inorganic azides. Subsequent introduction of azido and acetamido groups at C-2 of the sugar moiety and appropriate deprotection reactions involving excellent functional group tolerance with high stereo- and regioselectivity furnished ten 1,4-disubstituted and one 4-substituted 1,2,3-triazoles along with a 5-substituted tetrazole derivative with β-anomeric selectivity in good yields. The representative glycoconjugates displayed a high level of safety profile while tested in six cell lines using a cell viability assay. One of the compounds was also screened for aqueous solubility, liver microsomal stability across species, thereby demonstrating its pharmacologically relevant characteristics.

• Publication year

  2025

• Venue

  ACS Omega

• Publication date

  2025-08-27

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acsomega.5c02564PMID 40949193PMCID 12423807
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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