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Synthesis of the uridine LNA phosphoramidite. (a) i) NaH, BnBr, DMF, ii) acetic anhydride, pyridine, iii) 80% AcOH, iv) acetic anhydride, pyridine; (b) uracil, N,O-bis(trimethylsilyl)acetamide, TMS-triflate, acetonitrile; (c) NaOCH3, methanol; (d) i) p-toluenesulphonyl chloride, pyridine, ii) NaH, DMF; (e) H2, Pd(OH)2/C, ethanol; (f) DMTCI, pyridine; (g) ClP(NiPr2)(OCE), (iPr2)2NEt, dichloromethane. Bn = benzyl, Ac = acetyl. Adapted from [128].
