New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling

Kareem, Nuha S. and Mohammed, Shaymaa A. and Abed, May Jaleel and Aneed, Asaad H. and Kamal, Hayder M. and Mat Zahid, Nor Idayu and Sabah, Karem J. (2022) New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling. Journal of Carbohydrate Chemistry, 41 (1). pp. 1-17. ISSN 0732-8303, DOI

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A series of new macrocycles based on alkyl glycosides derived from D-glucose and D-galactose was synthesized. The macrocycles were easily obtained by the reaction of dialkynyl derivatives with diazides via copper-catlyzed 1,3-cycloaddition reaction. Simple protecting group strategies were applied to obtain the vicinal dihydroxy derivatives, followed by Williamson etherification with propargyl bromides to get the dialkynyl derivatives. These derivatives were subjected to 1,3-Huisgen triazole coupling with diazides furnishing the macrocycles in good yields. The 1,3-Huisgen reaction used to build these macrocycles was investigated thoroughly with respect to reaction time, catalysts, solvents, and temperature for optimum macrocyclisation.

Item Type: Article
Funders: Science and Technology Development Fund (STDF) Ministry of Higher Education & Scientific Research (MHESR) (FP036-2018A), Universiti Malaya [UM.C/625/1/HIR/MOHE/05]
Uncontrolled Keywords: Glycolipid; Macrocycle; Glucose; Galactose; 1; 3-dipolar cycloaddition; Copper
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history > QH301 Biology
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 08 Aug 2022 00:35
Last Modified: 08 Aug 2022 00:35

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