Multi-step reaction with 10 steps
1: 89 percent / DDC, DMAP / CH2Cl2 / 16 h / Ambient temperature
2: 78 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C
3: 83 percent / pyridine, DMAP / CHCl3 / 16 h / 40 °C
4: 78 percent / lithium azide, NaI / dimethylformamide / 16 h / 100 °C
5: POCl3, NEt3, 1.2.4-triazole / acetonitrile / 2 h / 0 - 20 °C
6: 99 percent / aq. NH3 / 1 h / 0 - 20 °C
7: 75 percent / pyridine / methanol / 4 h / Ambient temperature
8: H2 / Pd/C / methanol / 3 h / 750.06 Torr / Ambient temperature
9: pyridine / 16 h / Ambient temperature
10: LiOH*H2O / tetrahydrofuran; H2O / 6 h / Ambient temperature
With
pyridine; 1,2,4-Triazole; dmap; lithium hydroxide; ammonium hydroxide; lithium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; 2`,3`-dideoxycytidine; sodium iodide; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(99)00389-5