title: Design and Synthesis of Triazole-Linked xylo-Nucleoside Dimers.
abstract: Three triazole-linked nonionic xylo-nucleoside dimers T(L)-t-T(xL), T(L)-t-A(BzxL) and T(L)-t-C(BzxL) have been synthesized for the first time by Cu(I) catalyzed azide-alkyne [3 + 2] cycloaddition reaction (CuAAC) of 1-(3'-azido-3'-deoxy-2'-O,4'-C-methylene-β-D-ribo-furanosyl)thymine with different alkynes, i.e., 1-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylofuranosyl)thymine, 9-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylo-furanosyl)-N6-benzoyladenine and 1-(5'-deoxy-5'-C-ethynyl-2'-O,4'-C-methylene-β-D-xylofuranosyl)-N4-benzoylcytosine in 90%-92% yields. Among the two Cu(I) reagents, CuSO4.5H2O-sodium ascorbate in THF:(t)BuOH:H2O (1:1:1) and CuBr.SMe2 in THF used for cycloaddition (click) reaction, the former one was found to be better yielding than the latter one.
authors.affiliation: a Bioorganic Laboratory, Department of Chemistry , University of Delhi , Delhi , India.
authors.forename: Smriti
authors.initials: S
authors.lastname: Srivastava
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Singh
authors.forename: Vivek K
authors.initials: VK
authors.lastname: Sharma
authors.forename: Priyanka
authors.initials: P
authors.lastname: Mangla
authors.forename: Carl E
authors.initials: CE
authors.lastname: Olsen
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*; D014994:Xylose / Q000737:chemistry*
chemical_list: D011741:Pyrimidine Nucleosides; D014230:Triazoles; D014994:Xylose
keywords: Click chemistry; Huisgen-Sharpless-Meldal [3+2] cycloaddition; locked nucleic acid; phosphate backbone modification