alpha-半乳糖基-C16-神经酰胺合成路线 （共 31 条）
反应条件
1: 83 percent / Zn; NH4Cl / methanol 2: 76 percent / Hunig's base / CH2Cl2 3: 88 percent / HF*pyridine / acetonitrile / 10 h / 20 °C 4: 71 percent / BF3*Et2O / CH2Cl2 / 2 h 5: piperidine / dimethylformamide / 0.08 h 6: 7.1 mg / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 7: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH2Cl2 / 24 h / Heating 8: CF3CO2H / CH2Cl2; H2O / 12 h 9: 10.3 mg / NaOMe / methanol / 12 h View Scheme
参考文献
Rai, Anand Narain; Basu, Amit
Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 8228 - 8230
反应条件
1: 88 percent / HF*pyridine / acetonitrile / 10 h / 20 °C 2: 71 percent / BF3*Et2O / CH2Cl2 / 2 h 3: piperidine / dimethylformamide / 0.08 h 4: 7.1 mg / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 5: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH2Cl2 / 24 h / Heating 6: CF3CO2H / CH2Cl2; H2O / 12 h 7: 10.3 mg / NaOMe / methanol / 12 h View Scheme
参考文献
Rai, Anand Narain; Basu, Amit
Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 8228 - 8230
反应条件
1: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C 2: 89 percent / pyridine / 0.5 h / Ambient temperature 3: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 4: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 5: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi; Kosai; Arizuka; Watanabe; Fukunaga; Monden; Uchikoda; Yamagiwa; Kamikawa
Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1189 - 1192
反应条件
1: 89 percent / pyridine / 0.5 h / Ambient temperature 2: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 3: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 4: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi; Kosai; Arizuka; Watanabe; Fukunaga; Monden; Uchikoda; Yamagiwa; Kamikawa
Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1189 - 1192
反应条件
1: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 2: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 3: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi; Kosai; Arizuka; Watanabe; Fukunaga; Monden; Uchikoda; Yamagiwa; Kamikawa
Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1189 - 1192
反应条件
1: 72 percent / hydrochloric acid / tetrahydrofuran / 1 h / Heating 2: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C 3: 89 percent / pyridine / 0.5 h / Ambient temperature 4: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 5: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 6: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi; Kosai; Arizuka; Watanabe; Fukunaga; Monden; Uchikoda; Yamagiwa; Kamikawa
Tetrahedron Letters, 1988 , vol. 29, # 10 p. 1189 - 1192
反应条件
1: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH2Cl2 / 24 h / Heating 2: CF3CO2H / CH2Cl2; H2O / 12 h 3: 10.3 mg / NaOMe / methanol / 12 h View Scheme
参考文献
Rai, Anand Narain; Basu, Amit
Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 8228 - 8230
反应条件
1: 7.1 mg / Et3N; DMAP / CH2Cl2 / 1 h / 20 °C 2: 72 percent / Grubbs second-generation ruthenium carbene catalyst / CH2Cl2 / 24 h / Heating 3: CF3CO2H / CH2Cl2; H2O / 12 h 4: 10.3 mg / NaOMe / methanol / 12 h View Scheme
参考文献
Rai, Anand Narain; Basu, Amit
Journal of Organic Chemistry, 2005 , vol. 70, # 20 p. 8228 - 8230
反应条件
1: 95 percent / pyridine / Ambient temperature 2: 72 percent / hydrochloric acid / tetrahydrofuran / 1 h / Heating 3: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C 4: 89 percent / pyridine / 0.5 h / Ambient temperature 5: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 6: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 7: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi, Kinji; Kosai, Shunji; Arizuka, Mitsuo; Watanabe, Takashi; Yamagiwa, Yoshiro; et al.
Tetrahedron, 1989 , vol. 45, # 9 p. 2557 - 2570
反应条件
1: 95 percent / pyridine / Ambient temperature 2: 72 percent / hydrochloric acid / tetrahydrofuran / 1 h / Heating 3: 66 percent / imidazole / dimethylformamide / 13 h / 60 °C 4: 89 percent / pyridine / 0.5 h / Ambient temperature 5: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 6: 47 percent / 1,1,3,3-tetramethylurea, stannous triflate, 4A molecular sieves / CH2Cl2 / 16 h / Ambient temperature 7: 95 percent / sodium methoxide / methanol / 1 h / Ambient temperature View Scheme
参考文献
Ohashi, Kinji; Kosai, Shunji; Arizuka, Mitsuo; Watanabe, Takashi; Yamagiwa, Yoshiro; et al.
Tetrahedron, 1989 , vol. 45, # 9 p. 2557 - 2570
