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Schematic synthesis of the l-threoninol-thymine, the phoshoramidite and the functionalized solid support.
Reagents and conditions: (a) i: p-nitrophenol, DCC, pyridine 0 °C > RT O.N.; ii: l-threoninol, Et3N, DMF, RT O.N., 76%; (b) DMT-Cl, iPr2NEt, pyridine/DMF (4:2) RT 3 h, 76%; (c) i: succinic anhydride, DMAP, CH2Cl2, ii: LCAA-CPG, PPh3, DMAP, 2,2'-dithio-bis(5-nitropyridine), CH2Cl2/ACN; (d) 2-cyanoethoxy-N,N'-diisopropylaminochlorophosphine, iPr2NEt, CH2Cl2, RT, 91%.
