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. Author manuscript; available in PMC: 2018 Jan 9.
Published in final edited form as: Chem Commun (Camb). 2017 Jan 24;53(8):1389–1392. doi: 10.1039/c6cc08670e

Scheme 1.

Scheme 1

Chemical structure of eukaryotic thymidine modifications and synthesis of the 5-formyl-2′-deoxyuridine phosphoramidite. (A) Structure of 5hmU, 5fU and base J. (B) Synthesis of the 5fU phosphoramidite: (i) HO(CH2)3OH, TiCl4, (EtO)3CH, CH2Cl2, 0 °C, 1 h, 80%; (ii) HF·pyridine, THF, 0° to rt, 1 h, 99%; (iii) DMTrCl, Et3N, pyridine, rt, 4 h, 92%; (iv) ClPN(iPr)2(OCH2CH2CN), Et3N, 0 °C to rt, 3 h, 57%.