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. Author manuscript; available in PMC: 2018 Nov 29.

Published in final edited form as: Org Biomol Chem. 2017 Nov 29;15(46):9760–9774. doi: 10.1039/c7ob02152f

Scheme 1 — Original route to 2′-O-(pyren-1-yl)methyluridine phosphoramidite 5:¹⁰ (a) TrCl, pyridine (27%)¹¹; (b) (i) KOH, 1-chloromethylpyrene, benzene/dioxane, (ii) 80% aq. AcOH (65% from 2)¹⁰; (c) DMTr-Cl, DMAP, pyridine (72%);¹² (d) NC(CH₂)₂OP(Cl)N(i-Pr)₂, (i-Pr)₂NEt, CH₂Cl₂ (76%).¹²