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

Scheme 13.

Synthesis of 3'-C-phenyl d4A analogue 113.

Scheme 13

Reagents and Conditions: (i) Reference [30]; (ii) TBDMSCl, imidazole, DMF, 0 °C, 25 min, 88%; (iii) PivCl, iPr2NEt, CH2Cl2, 0 °C, 1.5 h, 97%; (iv) PhSH, NaOH, MeOH, reflux, 2.5 h, 90%; (v) MCBPA, MeOH, 0 °C, 2.5 h, 100%; (vi) (a) NH3, MeOH, 4 °C, 12 h; (b) MsCl, DMAP, pyridine, 0 °C then rt, 12 h, 81% for the two steps; (vii) Bu3SnH, AIBN, TEA, benzene, 80 °C, 5.5 h, 76%; (viii) PhI, Pd(PPh3)4 (10 mol %), CuI, DMF, rt, 28 h, 66%.