title: Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates.
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.
authors: Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
authors: Dhananjay
authors: D
authors: Kumar
authors: Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
authors: Kunj B
authors: KB
authors: Mishra
authors: Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
authors: Bhuwan B
authors: BB
authors: Mishra
authors: Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
authors: Saheli
authors: S
authors: Mondal
authors: Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India. Electronic address: vtiwari@ucdavis.edu.
authors: Vinod K
authors: VK
authors: Tiwari
mesh_terms: D057930:Click Chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D005003:Ethisterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006001:Glycoconjugates; D014230:Triazoles; D005003:Ethisterone
keywords: Carbohydrate; Click chemistry; Ethisterone; Glycoconjugate