(2S,5S)-2-[3-[[2-[(叔丁基二甲基硅)氧]乙基]磺酰基]-5-甲氧基-4-丙氧基苯基]-5-(3,4,5-三甲氧基苯基)四氢呋喃合成路线 （共 21 条）
反应条件
3-chloro-benzenecarboperoxoic acid in dichloromethane
T=20°C; 1 h;
参考文献
Shi, Hongxin; Liu, Huazhang; Bloch, Robert; Mandville, Gerard
Tetrahedron Asymmetry, 2002 , vol. 13, # 13 p. 1423 - 1428
反应条件
1: 90 percent / copper bronze / dimethylformamide / 22 h / 108 °C
2: 95 percent / magnesium monoperoxyphthalate / H2O; acetonitrile / 2 h / 50 °C
3: 95 percent / imidazole / dimethylformamide / 2 h / 25 °C
4: 97 percent / diisobutylaluminum hydride / toluene / 1 h / -70 °C
5: 1) Mg
View Scheme
参考文献
Thompson; Tschaen; Simpson; McSwine; Reamer; Verhoeven; Shinkai
Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7044 - 7052
反应条件
1: pyridinium p-toluenesulfonate / toluene / 0.75 h / 70 °C
2: 90 percent / copper bronze / dimethylformamide / 22 h / 108 °C
3: 95 percent / magnesium monoperoxyphthalate / H2O; acetonitrile / 2 h / 50 °C
4: 95 percent / imidazole / dimethylformamide / 2 h / 25 °C
5: 97 percent / diisobutylaluminum hydride / toluene / 1 h / -70 °C
6: 1) Mg
View Scheme
参考文献
Thompson; Tschaen; Simpson; McSwine; Reamer; Verhoeven; Shinkai
Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7044 - 7052
反应条件
1: 1) (-)-chlordiisopinocampheylborane, 2) 5 M aq. NaOH / 1) THF, a) 0 deg C, 4 h, b) 0-5 deg C, 2) methanol, water, 23 deg C, 1.5 h
2: pyridinium p-toluenesulfonate / toluene / 0.75 h / 70 °C
3: 90 percent / copper bronze / dimethylformamide / 22 h / 108 °C
4: 95 percent / magnesium monoperoxyphthalate / H2O; acetonitrile / 2 h / 50 °C
5: 95 percent / imidazole / dimethylformamide / 2 h / 25 °C
6: 97 percent / diisobutylaluminum hydride / toluene / 1 h / -70 °C
7: 1) Mg
View Scheme
参考文献
Thompson; Tschaen; Simpson; McSwine; Reamer; Verhoeven; Shinkai
Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7044 - 7052
反应条件
1: 95 percent / magnesium monoperoxyphthalate / H2O; acetonitrile / 2 h / 50 °C
2: 95 percent / imidazole / dimethylformamide / 2 h / 25 °C
3: 97 percent / diisobutylaluminum hydride / toluene / 1 h / -70 °C
4: 1) Mg
View Scheme
参考文献
Thompson; Tschaen; Simpson; McSwine; Reamer; Verhoeven; Shinkai
Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7044 - 7052
反应条件
1: 95 percent / imidazole / dimethylformamide / 2 h / 25 °C
2: 97 percent / diisobutylaluminum hydride / toluene / 1 h / -70 °C
3: 1) Mg
View Scheme
参考文献
Thompson; Tschaen; Simpson; McSwine; Reamer; Verhoeven; Shinkai
Journal of Organic Chemistry, 1992 , vol. 57, # 26 p. 7044 - 7052
反应条件
1.1: 96 percent / cesium carbonate / dimethylformamide / 2 h / 50 °C
2.1: 91 percent / 2-methyl-2-butene; aq. sodium chlorite; NaH2PO4 / 2-methyl-propan-2-ol / 4 h / 20 °C
3.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 18 h / 20 °C
4.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl3; AIBN / 0.08 h / Heating
5.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C
6.1: 92 percent / imidazole / dimethylformamide / 20 °C
7.1: t-BuLi / pentane / 0.5 h / -78 °C
7.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
8.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C
9.1: 67 percent / 450 °C / 0 Torr
10.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure
11.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Shi, Hongxin; Liu, Huazhang; Bloch, Robert; Mandville, Gerard
Tetrahedron Asymmetry, 2002 , vol. 13, # 13 p. 1423 - 1428
反应条件
1.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C
1.2: ClTi(O-i-Pr)3 / diethyl ether; pentane; hexane / -40 - 0 °C
1.3: 91 percent / tetrahydrofuran; diethyl ether; various solvents / 4.5 h / 0 - 20 °C
2.1: 78 percent / 4 Angstroem molecular sieves; 4-methoxymorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 5 h / 20 °C
3.1: t-BuLi / pentane / 0.5 h / -78 °C
3.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
4.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C
5.1: 67 percent / 450 °C / 0 Torr
6.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure
7.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Shi, Hongxin; Liu, Huazhang; Bloch, Robert; Mandville, Gerard
Tetrahedron Asymmetry, 2002 , vol. 13, # 13 p. 1423 - 1428
反应条件
1.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 18 h / 20 °C
2.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl3; AIBN / 0.08 h / Heating
3.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C
4.1: 92 percent / imidazole / dimethylformamide / 20 °C
5.1: t-BuLi / pentane / 0.5 h / -78 °C
5.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
6.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C
7.1: 67 percent / 450 °C / 0 Torr
8.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure
9.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Shi, Hongxin; Liu, Huazhang; Bloch, Robert; Mandville, Gerard
Tetrahedron Asymmetry, 2002 , vol. 13, # 13 p. 1423 - 1428
反应条件
1.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C
2.1: 92 percent / imidazole / dimethylformamide / 20 °C
3.1: t-BuLi / pentane / 0.5 h / -78 °C
3.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C
4.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C
5.1: 67 percent / 450 °C / 0 Torr
6.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure
7.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C
View Scheme
参考文献
Shi, Hongxin; Liu, Huazhang; Bloch, Robert; Mandville, Gerard
Tetrahedron Asymmetry, 2002 , vol. 13, # 13 p. 1423 - 1428
