甲基 3,6-二-O-苄基-2-脱氧-2-(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)吡喃己糖苷合成路线 (共 22 条)
反应条件
1.1: pyridine / 0 - 20 °C
2.1: boron trifluoride diethyl etherate / chloroform / 0.17 h / 0 - 20 °C / Inert atmosphere
2.2: 2 h / 20 °C / Inert atmosphere
3.1: methanol; sodium methylate / 1.5 h / 20 °C / pH 9
4.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
7.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1.1: methanol; sodium methylate / 1.5 h / 20 °C / pH 9
2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
5.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1.1: sodium hydroxide / water / 20 °C
2.1: pyridine / 0 - 20 °C
3.1: boron trifluoride diethyl etherate / chloroform / 0.17 h / 0 - 20 °C / Inert atmosphere
3.2: 2 h / 20 °C / Inert atmosphere
4.1: methanol; sodium methylate / 1.5 h / 20 °C / pH 9
5.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
8.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
3.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 - 50 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
4.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1: hydrogenchloride; sodium cyanoborohydride / tetrahydrofuran; diethyl ether / 5 h / 0 - 20 °C / Molecular sieve
2: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
参考文献
Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran
Organic and Biomolecular Chemistry, 2012 , vol. 10, # 15 p. 3019 - 3032
反应条件
1: 1.) HgO, HgCl2, Drierite / 1.) dichloromethane, 1 h, r.t. 2.) 48 h
2: sodium methoxide, methanol / dioxane / 1 h / Ambient temperature
3: 4-toluenesulfonic acid / acetonitrile / 12 h / Ambient temperature
4: 1.) sodium hydride / 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t.
5: 70 percent / NaBH3CN, 3 Angstroem molecular sieves, HCl / tetrahydrofuran; diethyl ether / 5 h / Ambient temperature
View Scheme
参考文献
Alais, Jocelyne; David, Serge
Carbohydrate Research, 1990 , vol. 201, # 1 p. 69 - 77
反应条件
1: 85 percent / p-toluenesulphonic acid / acetonitrile
2: 86 percent / sodium hydride / 1,2-dimethoxy-ethane
3: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature
View Scheme
参考文献
Schwartz; Lee; Carver; Krepinsky
Canadian Journal of Chemistry, 1985 , vol. 63, # 5 p. 1073 - 1079
反应条件
1: 86 percent / sodium hydride / 1,2-dimethoxy-ethane
2: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature
View Scheme
参考文献
Schwartz; Lee; Carver; Krepinsky
Canadian Journal of Chemistry, 1985 , vol. 63, # 5 p. 1073 - 1079
反应条件
1: 95 percent / silver zeolite / CH2Cl2 / 1 h / Ambient temperature
2: 85 percent / sodium methoxide / methanol
3: 85 percent / p-toluenesulphonic acid / acetonitrile
4: 86 percent / sodium hydride / 1,2-dimethoxy-ethane
5: 95 percent / molecular sieves, sodium cyanoborohydride, HCl / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature
View Scheme
参考文献
Schwartz; Lee; Carver; Krepinsky
Canadian Journal of Chemistry, 1985 , vol. 63, # 5 p. 1073 - 1079