New macrocycles incorporating glycolipids via copper-catalyzed triazole coupling
Document Type
Article
Publication Date
1-2-2022
Abstract
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.
Keywords
Glycolipid, Macrocycle, Glucose, Galactose, 1, 3-dipolar cycloaddition, Copper
Divisions
CHEMISTRY
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]
Publication Title
Journal of Carbohydrate Chemistry
Volume
41
Issue
1
Publisher
Taylor & Francis Inc
Publisher Location
530 WALNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA