5-叠氮基-6-(叔-丁基二甲基硅烷基)-2,3-O-异亚丙基L-古洛糖酸-1,4-内酯合成路线 （共 9 条）
反应条件
hydrogen azide; triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran; toluene T=20°C; Mitsunobu reaction; 20 h;
参考文献
Hering, Kirk W.; Karaveg, Khanita; Moremen, Kelley W.; Pearson, William H.
Journal of Organic Chemistry, 2005 , vol. 70, # 24 p. 9892 - 9904
反应条件
sodium azide in N,N-dimethyl-formamide Yield given;
参考文献
Tetrahedron Letters, , vol. 29, # 23 p. 2871 - 2874
反应条件
1: 79 percent / acetic acid / H2O / 16 h / 30 °C 2: 71 percent / imidazole / dimethylformamide / 2 h / -40 °C 3: pyridine; CH2Cl2 / 1 h / -30 °C 4: NaN3 / dimethylformamide / 3 h View Scheme
参考文献
Tetrahedron, , vol. 45, # 1 p. 319 - 326
反应条件
1: 71 percent / imidazole / dimethylformamide / 2 h / -40 °C 2: pyridine; CH2Cl2 / 1 h / -30 °C 3: NaN3 / dimethylformamide / 3 h View Scheme
参考文献
Tetrahedron, , vol. 45, # 1 p. 319 - 326
反应条件
1: 79 percent / p-toluenesulfonic acid / acetone / 36 h 2: 79 percent / acetic acid / H2O / 16 h / 30 °C 3: 71 percent / imidazole / dimethylformamide / 2 h / -40 °C 4: pyridine; CH2Cl2 / 1 h / -30 °C 5: NaN3 / dimethylformamide / 3 h View Scheme
参考文献
Tetrahedron, , vol. 45, # 1 p. 319 - 326
→
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: 89 percent / sodiumborohydride / ethanol / 4 h / 20 °C 2: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C 3: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 4: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 5: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 6: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C 7: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 8: 13 mg / NH3 / methanol / 24 h / 20 °C 9: 80 percent / trifluoroacetic acid / H2O View Scheme
参考文献
Hering, Kirk W.; Karaveg, Khanita; Moremen, Kelley W.; Pearson, William H.
Journal of Organic Chemistry, 2005 , vol. 70, # 24 p. 9892 - 9904
→
134234-43-8(3aS,3bR,7aR,11aS,11bR)-2,2,5,5-四甲基六氢-3bH-[1,3]二恶英并[4,5-e][1,3]二氧杂环戊并[4,5-c]咪唑并[1,2-a]吡啶-9,10-二酮
反应条件
1: 89 percent / sodiumborohydride / ethanol / 4 h / 20 °C 2: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C 3: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 4: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 5: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 6: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C 7: Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C 8: 13 mg / NH3 / methanol / 24 h / 20 °C View Scheme
参考文献
Hering, Kirk W.; Karaveg, Khanita; Moremen, Kelley W.; Pearson, William H.
Journal of Organic Chemistry, 2005 , vol. 70, # 24 p. 9892 - 9904
反应条件
1: 91 percent / H2 / 10percent Pd/C / methanol / 14 h 2: 89 percent / trifluoroacetic acid / H2O / 1 h View Scheme
参考文献
Fleet, George W. J.; Ramsden, Nigel G.; Witty, David R.
Tetrahedron Letters, 1988 , vol. 29, # 23 p. 2871 - 2874
反应条件
1: 89 percent / sodiumborohydride / ethanol / 4 h / 20 °C 2: 79 percent / pyridine / CH2Cl2 / 20 h / 20 °C 3: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C 4: 97 percent / p-toluenesulfonic acid / CH2Cl2 / 0.25 h / 20 °C 5: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C 6: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C View Scheme
参考文献
Hering, Kirk W.; Karaveg, Khanita; Moremen, Kelley W.; Pearson, William H.
Journal of Organic Chemistry, 2005 , vol. 70, # 24 p. 9892 - 9904
