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.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h
2: 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
1: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature
2: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h
3: 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
1: 95 percent / HCl, H2O
2: 97 percent / pyridine
3: 66 percent / Me3SiOTf / CH2Cl2
4: NH3 / methanol
5: NaH / dimethylformamide
6: 1.) HMDS, 2.) NBS, molecular sieves 4 Angstroem / 2.) CH2Cl2
7: 12 percent / H2 / Pd(OH)2/C / ethanol
View Scheme
参考文献
Nielsen, Poul; Wengel, Jesper
Chemical Communications, 1998 , # 23 p. 2645 - 2646
反应条件
1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating
1.2: 88 percent / trimethylsilyl triflate / acetonitrile / 4 h / Heating
2.1: 94 percent / aq. NaOH / dioxane; H2O / 1 h / 20 °C
3.1: 86 percent / dimethylformamide / 5 h / 100 °C
4.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h
5.1: 83 percent / HCO2NH4 / Pd(OH)2/C / methanol / 0.17 h / Heating
View Scheme
参考文献
Koshkin; Fensholdt; Pfundheller; Lomholt
Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8504 - 8512
反应条件
1: 86 percent / dimethylformamide / 5 h / 100 °C
2: 91 percent / aq. NaOH / tetrahydrofuran / 1 h
3: 83 percent / HCO2NH4 / Pd(OH)2/C / methanol / 0.17 h / Heating
View Scheme
参考文献
Koshkin; Fensholdt; Pfundheller; Lomholt
Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8504 - 8512
反应条件
1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h
2: 83 percent / HCO2NH4 / Pd(OH)2/C / methanol / 0.17 h / Heating
View Scheme
参考文献
Koshkin; Fensholdt; Pfundheller; Lomholt
Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8504 - 8512
反应条件
1: 94 percent / aq. NaOH / dioxane; H2O / 1 h / 20 °C
2: 86 percent / dimethylformamide / 5 h / 100 °C
3: 91 percent / aq. NaOH / tetrahydrofuran / 1 h
4: 83 percent / HCO2NH4 / Pd(OH)2/C / methanol / 0.17 h / Heating
View Scheme
参考文献
Koshkin; Fensholdt; Pfundheller; Lomholt
Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8504 - 8512
反应条件
1: 5-bromo-2'-O,4'-C-methyleneuridine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane
Heating;
2: trimethylaluminum With triphenylphosphine; palladium dichloride in tetrahydrofuran
Heating;
3: With ammonium chloride in methanol; water
Heating;
参考文献
Obika; Hari; Sugimoto; Sekiguchi; Imanishi
Tetrahedron Letters, 2000 , vol. 41, # 46 p. 8923 - 8927
反应条件
1: 1,1,1,3,3,3-hexamethyl-disilazane; 5-bromo-2'-O,4'-C-methyleneuridine With ammonium sulfate
24 h; Heating;
2: trimethylaluminum With triphenylphosphine; palladium dichloride in tetrahydrofuran; hexane
67 h; Heating;
3: With ammonium chloride in methanol
5 h; Heating;
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: 75 percent / NaBH3CN; TiCl4 / acetonitrile / 15 h / 0 °C
2.1: 61 percent / NaN(SiMe3)2 / tetrahydrofuran / 3 h / 20 °C
3.1: 100 percent / H2 / Pd/C / methanol / 15 h / 20 °C
4.1: 84 percent / NaN3; NBS / 1,2-dimethoxy-ethane; H2O / 27 h / 20 °C
5.1: (NH4)2SO4 / 24 h / Heating
5.2: PdCl2; PPh3 / tetrahydrofuran; hexane / 67 h / Heating
5.3: 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
