Kumar Dhananjay, Mishra Kunj B, Mishra Bhuwan B, Mondal Saheli, Tiwari Vinod K
Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 221005, India.
Steroids. 2014 Feb;80:71-9. doi: 10.1016/j.steroids.2013.11.022. Epub 2013 Dec 5.
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.
通过对甲苯磺酰基/溴代糖与叠氮化钠在干燥的N,N-二甲基甲酰胺中加热条件下反应制备了多种脱氧叠氮糖3。研究了在二氯甲烷中碘化亚铜和N,N-二异丙基乙胺存在下或在水介质中五水硫酸铜和抗坏血酸钠存在下，脱氧叠氮糖3与炔诺酮4进行1,3-偶极环加成反应以得到区域选择性三唑连接的炔诺酮糖缀合物5。所有合成的化合物均通过光谱分析（红外光谱、氢核磁共振谱、碳核磁共振谱和质谱）进行了表征。三唑基炔诺酮糖缀合物5a的结构通过单晶X射线分析得到了进一步确证。
