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Paper | Regular issue | Vol 96, No. 1, 2018, pp.106-126
Published online, 14th December, 2017
DOI: 10.3987/COM-17-13837
Synthesis of Triazol Cn-Ribonucleoside Phosphoramidites Using β-Ribofuranosyl-Cn-acetylenes for RNA Catalysis Probing

Hiroki Yoneyama, Fumiko Hikasa, Daiki Fujisue, Yoshihide Usami, Zheng-yun Zhao, and Shinya Harusawa*

*Department of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


Novel C4-linked triazol C0-, C1- and C2-ribonucleoside phosphoramidites for RNA catalysis probing were synthesized from β-ribofuranosyl-Cn-acetylenes (n = 0–2), which were efficiently prepared by fragmentation of tetrazoles derived from cyanophosphates. N-Pivaloyloxymethyl moiety was selected for the protection of triazole-N, whose properties under acidic and basic conditions were investigated.