异丙基-2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖苷合成路线 （共 22 条）
反应条件
1: Et3N; MeSiCl3 / tetrahydrofuran / 24 h / 60 °C
2: 31 mg / H2O / tetrahydrofuran / 0.5 h
3: 100 percent / pyridine / 2 h / 20 °C
View Scheme
参考文献
Yeung; Adamski-Werner; Bernard; Poulenat; Petillo
Organic letters, 2000 , vol. 2, # 20 p. 3135 - 3138
反应条件
1: pyridine
2: 82 percent / 33percent hydrobromic acid / CH2Cl2; acetic acid / 0.5 h / 0 °C
3: 87 percent / acetic acid / 0.75 h / Ambient temperature
4: 95 percent / 5 Angstroem molecular sieves / trimethylsilyl triflate / CH2Cl2 / 12 h / -35 °C
5: dimethyl malonate / Pd(PPh3)4 / tetrahydrofuran / 24 h / Ambient temperature
6: pyridine
View Scheme
参考文献
Boullanger, Paul; Banoub, Joseph; Descotes, Gerard
Canadian Journal of Chemistry, 1987 , vol. 65, p. 1343 - 1348
反应条件
1: 1.) NaOMe; 2.) Et3N / 1.) MeOH, r.t., 10 min; 2.) MeOH, r.t., 3 h
2: pyridine
3: 82 percent / 33percent hydrobromic acid / CH2Cl2; acetic acid / 0.5 h / 0 °C
4: 87 percent / acetic acid / 0.75 h / Ambient temperature
5: 95 percent / 5 Angstroem molecular sieves / trimethylsilyl triflate / CH2Cl2 / 12 h / -35 °C
6: dimethyl malonate / Pd(PPh3)4 / tetrahydrofuran / 24 h / Ambient temperature
7: pyridine
View Scheme
参考文献
Boullanger, Paul; Banoub, Joseph; Descotes, Gerard
Canadian Journal of Chemistry, 1987 , vol. 65, p. 1343 - 1348
反应条件
1: 87 percent / acetic acid / 0.75 h / Ambient temperature
2: 95 percent / 5 Angstroem molecular sieves / trimethylsilyl triflate / CH2Cl2 / 12 h / -35 °C
3: dimethyl malonate / Pd(PPh3)4 / tetrahydrofuran / 24 h / Ambient temperature
4: pyridine
View Scheme
参考文献
Boullanger, Paul; Banoub, Joseph; Descotes, Gerard
Canadian Journal of Chemistry, 1987 , vol. 65, p. 1343 - 1348
反应条件
1: 82 percent / 33percent hydrobromic acid / CH2Cl2; acetic acid / 0.5 h / 0 °C
2: 87 percent / acetic acid / 0.75 h / Ambient temperature
3: 95 percent / 5 Angstroem molecular sieves / trimethylsilyl triflate / CH2Cl2 / 12 h / -35 °C
4: dimethyl malonate / Pd(PPh3)4 / tetrahydrofuran / 24 h / Ambient temperature
5: pyridine
View Scheme
参考文献
Boullanger, Paul; Banoub, Joseph; Descotes, Gerard
Canadian Journal of Chemistry, 1987 , vol. 65, p. 1343 - 1348
反应条件
1: dimethyl malonate / Pd(PPh3)4 / tetrahydrofuran / 24 h / Ambient temperature
2: pyridine
View Scheme
参考文献
Boullanger, Paul; Banoub, Joseph; Descotes, Gerard
Canadian Journal of Chemistry, 1987 , vol. 65, p. 1343 - 1348
反应条件
1: 72 percent / K2CO3 / acetone; toluene / 1 h / 50 °C
2: 81 percent / 4 Angstroem molecular sieves, methyl iodide / CH2Cl2 / 22 h / 50 °C / stereochemistry, activation by methyl iodide; other acceptors
View Scheme
参考文献
Mereyala; Gurijala
Carbohydrate Research, 1993 , vol. 242, p. 277 - 280
反应条件
1: 58 percent / IN3 / acetonitrile / 2 h / 0 °C
2: 1.) triphenyl phosphine, 2.) DOWEX 2x8 resin, 3.) NaOMe, 4.) pyridine / 1.) CH2Cl2, 2.) methanol
View Scheme
参考文献
Lafont, Dominique; Guilloux, Pascal; Descotes, Gerard
Carbohydrate Research, 1989 , vol. 193, p. 61 - 74
反应条件
1.1: montmorillonite K-10 / 24 h / 0 °C
2.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 0.92 h / 50 °C
3.1: copper dichloride / toluene
3.2: 2.25 h / 62 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Wipf, Peter; Neal, Matthew D.; Chhinder, Sodhi P.; Hackam, David J.
Patent: US2013/281395 A1, 2013 ;
反应条件
1: potassium carbonate / acetonitrile / 20 °C
2: cobalt(II) chloride / dichloromethane / 6 h / 50 °C
View Scheme
参考文献
Kuryanov; Luschtshyk; Chupakhina
Russian Journal of Bioorganic Chemistry, 2013 , vol. 39, # 4 p. 426 - 433
Biokhimiya (Moscow), 2013 , vol. 39, # 4 p. 477 - 485
