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. 2013 Dec 4;56(24):10079–10102. doi: 10.1021/jm401497a

Scheme 14. Synthesis of Cyclopentyl-8-Ph-ADP.

Scheme 14

Reagents and conditions: (i) Br2, NaOAc buffer, 89%; (ii) Na2Cl4Pd, PhB(OH)2, TPPTS, Na2CO3, MeCN–H2O, 80 °C, 1h, 81%; (iii) 75% aq TFA, rt; (iv) POCl3, TEP, 0 °C, 1 h; (v) morpholine, PPh3, dipyridyldisulfide, DMSO, rt, 1 h then cyclopentylphosphate 79, MnCl2 in formamide, MgSO4, rt, 16 h, 12%.