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. 2020 Sep 24;11(41):11322–11330. doi: 10.1039/d0sc04520a

Scheme 2. Synthesis of 2′-OCF3 adenosine building block A7. Reaction conditions: (a) 1.1 equiv. TIPDSCl2, in pyridine, room temperature, 5 h, 95%; (b) 1.2 equiv. tBuLi, 9.0 equiv. CS2, 3.0 equiv. CH3I, in THF, −75 °C to room temperature, 18 h, 74%; (c) 2.5 equiv. benzoylchloride, 6 equiv. NH3, in pyridine, room temperature, 16 h, 89%; (d) 5.0 equiv. NBS, in HF pyridine and CH2Cl2, –75 °C to 0 °C, 3 h, 26%; (e) 1.5 equiv. DMTCl, 0.5 equiv. DMAP, in pyridine, room temperature, 16 h, 88%; (f) 2.5 equiv. 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, 7.5 equiv. iPr2NEt, 0.5 equiv. 1-methylimidazole, in CH2Cl2, room temperature, 2 h, 82%.

Scheme 2