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. 2014 Sep 2;42(16):10870. doi: 10.1093/nar/gku669

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© The Author(s) 2014. Published by Oxford University Press on behalf of Nucleic Acids Research.

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted reuse, distribution, and reproduction in any medium, provided the original work is properly cited.

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Scheme 1. — Synthesis of dimeric r(U_AM1U) and r(U_AM1A) phosphoramidites.^a ^aSteps: (a) TFA, THF, H₂O 0 °C, 4 h, 92%; (b) p-methoxytrityl chloride, pyridine, 0 °C to rt, 14 h, 85%; (c) OsO₄, 4-methylmorpholine N-oxide, dioxane, rt, 10 h, then NaIO₄ in water, rt, 12 h, 95%; (d) NaClO₄, NaH₂PO₄, 2-methylbut-2-ene, t-BuOH, THF water, rt, 1 h, 82%; (e) DIEA, Bu₂SnCl₂, dichloroethane, rt, 1 h, then add TOM-Cl, 80 °C, 45 min, 39%; (f) H₂S, pyridine, water, rt, 14 h 93%; (g) HBTU, HOBt, DIEA, CH₂Cl₂, rt, 12 h, 95% 11a, 86% 11b; (h) DIEA, ClP(OCH₂CH₂CN)N(iPr)₂, CH₂Cl₂, rt, 7 h, 71% 11a, 60% 11b.