1-(2’-O,4-C-甲桥-beta-D-呋喃核糖基)胸腺嘧啶合成路线 （共 33 条）
反应条件
1.1: 94 percent / aq. TFA / 0.17 h / 20 °C
2.1: 80 percent / ZnCl2 / 5 h / 20 °C
3.1: 75 percent / NaBH3CN; TiCl4 / acetonitrile / 15 h / 0 °C
4.1: 61 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / 20 °C
5.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
6.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
7.1: (NH4)2SO4 / 24 h / Heating
7.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
7.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
2.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
3.1: (NH4)2SO4 / 24 h / Heating
3.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
3.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1.1: 80 percent / ZnCl2 / 5 h / 20 °C
2.1: 75 percent / NaBH3CN; TiCl4 / acetonitrile / 15 h / 0 °C
3.1: 61 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / 20 °C
4.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
5.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
6.1: (NH4)2SO4 / 24 h / Heating
6.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
6.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1.1: 61 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / 20 °C
2.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
3.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
4.1: (NH4)2SO4 / 24 h / Heating
4.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
4.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1.1: 69 percent / pyridine / 3 h / 110 °C
2.1: 94 percent / aq. TFA / 0.17 h / 20 °C
3.1: 80 percent / ZnCl2 / 5 h / 20 °C
4.1: 75 percent / NaBH3CN; TiCl4 / acetonitrile / 15 h / 0 °C
5.1: 61 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / 20 °C
6.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
7.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
8.1: (NH4)2SO4 / 24 h / Heating
8.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
8.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH3CN, reflux, 1 h, 2.) 65 deg C, 2 h
2: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature
3: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h
4: 98 percent / H2 / Pd(OH)2/C / ethanol / 4 h / Ambient temperature
View Scheme
参考文献
Koshkin, Alexei A.; Singh, Sanjay K.; Nielsen, Poul; Rajwanshi, Vivek K.; Kumar, Ravindra; Meldgaard, Michael; Olsen, Carl Erik; Wengel, Jesper
Tetrahedron, 1998 , vol. 54, # 14 p. 3607 - 3630
反应条件
hydrogen; palladium dihydroxide in ethanol; dichloromethane
Hydrogenolysis;
参考文献
Nielsen, Poul; Wengel, Jesper
Nucleosides and Nucleotides, 1999 , vol. 18, # 4-5 p. 701 - 702
反应条件
1.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
2.1: (NH4)2SO4 / 24 h / Heating
2.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
2.3: 57 percent / aq. NH4Cl / methanol / 5 h / Heating
View Scheme
参考文献
Obika; Uneda; Sugimoto; Nanbu; Minami; Doi; Imanishi
Bioorganic and medicinal chemistry, 2001 , vol. 9, # 4 p. 1001 - 1011
反应条件
1: 80percent aq. AcOH
2: pyridine
3: 92 percent / N,O-bis(trimethylsilyl)acetamide, trimethylsilyl triflate / acetonitrile
4: 87 percent / NH3 / methanol / 4 h / Ambient temperature
5: 92 percent / NaH / dimethylformamide / 37 h / 0 °C
6: debenzylation
View Scheme
参考文献
Koshkin, Alexei A.; Rajwanshi, Vivek K.; Wengel, Jesper
Tetrahedron Letters, 1998 , vol. 39, # 24 p. 4381 - 4384
反应条件
1: 92 percent / N,O-bis(trimethylsilyl)acetamide, trimethylsilyl triflate / acetonitrile
2: 87 percent / NH3 / methanol / 4 h / Ambient temperature
3: 92 percent / NaH / dimethylformamide / 37 h / 0 °C
4: debenzylation
View Scheme
参考文献
Koshkin, Alexei A.; Rajwanshi, Vivek K.; Wengel, Jesper
Tetrahedron Letters, 1998 , vol. 39, # 24 p. 4381 - 4384
