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. 2008 Oct 16;36(20):6548–6557. doi: 10.1093/nar/gkn703

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© 2008 The Author(s)

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Figure 2. — Synthesis of the 5-formylcytidine phosphoramidite. The starting compound cytidine is numbered compound 1, intermediates are numbered 2–8 and the protected f⁵C phosphoramidite is compound 9. The synthetic transformations are: (a) acetone, dimethoxypropane, cat HClO₄ (83%); (b) paraformaldehyde, 0.5 M KOH, 55°C (38%, 60% brsm); (c) RuO₂ xH₂O, dioxane, reflux (82%); (d) 1 M HCl (95%); (e) TIPDSCl₂, Pyr, DMF; (f) DBF-CH(OMe)₂, DMF (71% over 2 steps); (g) ACE-orthoester, PPTS, TBDMS-pentanedione, DCM; (h) HF-TEMED, CH₃CN (53% over 2 steps); (i) BZH-Cl, DIA, DCM (84%); (j) P(OMe)(DIA)₂, DIA, S-Et Tetrazole, DCM (93%).