Novel triazolyl macrocycles incorporating glycolipids: a new protocol
الباحث الأول:
Hawraa Mohammed Sadiq
الباحثين الآخرين:
Karem J. Sabah * , Nuha S. Kareem , Wesam S. Kurdi , Shiemaa A. Mohammed , N. Idayu Zahid c
المجلة:
Carbohydrate Research
تاريخ النشر:
10 فبراير، 2025
مختصر البحث:
Six new macrocycles incorporating glycolipids containing one triazole ring in their structures were synthesized
via intramolecular macrocyclic closure. The synthesis strategy is based on the different reactivities of primary
and secondary hydroxyl…
Six new macrocycles incorporating glycolipids containing one triazole ring in their structures were synthesized
via intramolecular macrocyclic closure. The synthesis strategy is based on the different reactivities of primary
and secondary hydroxyl groups on the monosaccharides. The protecting of hydroxyls on 4,6-positions by benzylidene,
followed by benzylation of 2,3-positions and removal of the benzylidene, selectively left over the free
secondary and primary hydroxyl on 4- and 6-carbons, respectively. The selective tosylation on the primary
hydroxyl group followed by azide replacement prepares the first functionality of the glycolipids on carbon
number 6 (C-6) on the ring of monosaccharide moieties. Subsequently, the nucleophilic displacement of suitable
ethylene glycolic propargyl on the carbon number 4 (C-4) makes the intramolecular 1,3-dipolar ring closure
assisted via copper(I)-catalyzed azide-alkyne cycloaddition to be possible. All reaction conditions of 1,3-dipolar
ring closures, including time, catalyst, temperature, and solvent, have been optimized.
