Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

Dhananjay Kumar; Kunj B Mishra; Bhuwan B Mishra; Saheli Mondal; Vinod K Tiwari

doi:10.1016/j.steroids.2013.11.022

Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates

Steroids. 2014 Feb:80:71-9. doi: 10.1016/j.steroids.2013.11.022. Epub 2013 Dec 5.

Authors

Dhananjay Kumar¹, Kunj B Mishra¹, Bhuwan B Mishra¹, Saheli Mondal¹, Vinod K Tiwari²

Affiliations

¹ Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
² Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India. Electronic address: vtiwari@ucdavis.edu.

PMID: 24316164
DOI: 10.1016/j.steroids.2013.11.022

Abstract

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.

Keywords: Carbohydrate; Click chemistry; Ethisterone; Glycoconjugate.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Click Chemistry*
Crystallography, X-Ray
Cyclization
Ethisterone / analogs & derivatives*
Ethisterone / chemical synthesis
Ethisterone / chemistry
Glycoconjugates / chemical synthesis*
Glycoconjugates / chemistry
Models, Molecular
Molecular Conformation
Triazoles / chemical synthesis*
Triazoles / chemistry

Substances

Glycoconjugates
Triazoles
Ethisterone