Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates.
Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4·5H2O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, (1)H &(13)C NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis.
['Kumar|Dhananjay|D|', 'Mishra|Kunj B|KB|', 'Mishra|Bhuwan B|BB|', 'Mondal|Saheli|S|', 'Tiwari|Vinod K|VK|']
D057930:Click Chemistry D018360:Crystallography, X-Ray D003500:Cyclization D005003:Ethisterone D006001:Glycoconjugates D008958:Models, Molecular D008968:Molecular Conformation D014230:Triazoles
Click chemistry Ethisterone Glycoconjugate Carbohydrate