New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling
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...
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my.um.eprints.333432022-08-08T00:35:51Z http://eprints.um.edu.my/33343/ New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling Kareem, Nuha S. Mohammed, Shaymaa A. Abed, May Jaleel Aneed, Asaad H. Kamal, Hayder M. Mat Zahid, Nor Idayu Sabah, Karem J. QD Chemistry QH301 Biology 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. Taylor & Francis Inc 2022-01-02 Article PeerReviewed 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 https://doi.org/10.1080/07328303.2022.2039685 <https://doi.org/10.1080/07328303.2022.2039685>. 10.1080/07328303.2022.2039685 |
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QD Chemistry QH301 Biology Kareem, Nuha S. Mohammed, Shaymaa A. Abed, May Jaleel Aneed, Asaad H. Kamal, Hayder M. Mat Zahid, Nor Idayu Sabah, Karem J. New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
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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. |
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Article |
author |
Kareem, Nuha S. Mohammed, Shaymaa A. Abed, May Jaleel Aneed, Asaad H. Kamal, Hayder M. Mat Zahid, Nor Idayu Sabah, Karem J. |
author_facet |
Kareem, Nuha S. Mohammed, Shaymaa A. Abed, May Jaleel Aneed, Asaad H. Kamal, Hayder M. Mat Zahid, Nor Idayu Sabah, Karem J. |
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Kareem, Nuha S. |
title |
New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
title_short |
New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
title_full |
New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
title_fullStr |
New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
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New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
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new macrocycles incorporating glycolipids via copper-catalyzed triazole coupling |
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Taylor & Francis Inc |
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2022 |
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http://eprints.um.edu.my/33343/ |
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1740826023196360704 |
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