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Paper | Special issue | Vol 95, No. 1, 2017, pp.342-352
Published online, 7th October, 2016
DOI: 10.3987/COM-16-S(S)24
Synthesis of the 5-Methyluridine Monomer of 3’-O,4’-C-Ethyleneoxy-Bridged Nucleic Acid

Takashi Osawa, Masakazu Dohi, Yuka Hitomi, Yuta Ito, Satoshi Obika,* and Yoshiyuki Hari*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan

Abstract

A novel bridged nucleic acid, 3ʹ-O,4ʹ-C-ethyleneoxy-bridged nucleic acid (3ʹ,4ʹ-EoNA), forming 2ʹ,5ʹ-linkage with the flanking nucleotides in oligonucleotides was designed. The 3ʹ,4ʹ-EoNA is expected to improve the biophysical properties of the oligonucleotides (e.g., binding affinity with complementary single-stranded oligonucleotides and resistance against nuclease digestion) because of the presence of the 6ʹ-oxygen atom. In this study, the synthesis of the 5-methyluridine monomer of 3ʹ,4ʹ-EoNA was achieved via Lewis acid-mediated C4ʹ-iodoethoxylation followed by intramolecular 1,4-dioxane ring formation. Here, we describe, in detail, the results of the study.