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. 2015 Mar 18;20(3):4967–4997. doi: 10.3390/molecules20034967

Scheme 12.

Synthesis of 3'-C-phenyl d4U analogue 104.

Scheme 12

Reagents and Conditions: (i) Reference [28]; (ii) (PhSe)2, EtOH, NaBH4, THF, reflux, 48 h, 81%; (iii) aq NaOH (1N), EtOH, rt, 24 h; (iv) TBDMSCl, pyridine, rt, 24 h, 96% for the two steps; (v) imidazole, SOBr2, CCl4, rt, 6 h; (vi) MCPBA, rt, 12 h, 102: 38%, 103: 42% for the two steps; (vii) Ph4Sn, (Ph3P)2PdCl2 (10 mol %), TEA, DMF, 100 °C, 24 h, 39%.