Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

• Cu-catalyzed azide–alkyne cycloaddition to form regioselective novel conjugates has emerged as a fast growing technology.
• Click chemistry inspired highly facile syntheses of triazolyl ethisterone glycoconjugate have been discussed.
• The reaction time under microwave heating has been significantly reduced to 10 min.

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, 1H & 13C NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis.

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