(5S)-5,7-二-{[叔-丁基二甲基硅烷基)氧基]}-4,4-二甲基庚烷-3-酮合成路线 （共 50 条）
反应条件
1: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1) -78 deg C, 5 min, 2) 0 deg C, 15 min
2: 1.26 g / Et3N, 4-DMAP / CH2Cl2 / 1) 0 deg C, 2 h, 2) 25 deg C, 10 h
View Scheme
参考文献
Nicolaou; Ninkovic; Sarabia; Vourloumis; He; Vallberg; Finlay; Yang
Journal of the American Chemical Society, 1997 , vol. 119, # 34 p. 7974 - 7991
反应条件
1: 93 percent / 1 h / -78 - 0 °C
2: 93 percent / NaH / toluene; tetrahydrofuran / 1 h / 0 - 20 °C
3: 99 percent / DIBAl-H / diethyl ether / 3 h / 0 - 20 °C
4: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C
5: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
6: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
7: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
8: 97 percent / 1 h / -78 - 0 °C
9: 82 percent / diethyl ether / 0.5 h / 0 °C
10: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 93 percent / NaH / toluene; tetrahydrofuran / 1 h / 0 - 20 °C
2: 99 percent / DIBAl-H / diethyl ether / 3 h / 0 - 20 °C
3: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C
4: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
5: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
6: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
7: 97 percent / 1 h / -78 - 0 °C
8: 82 percent / diethyl ether / 0.5 h / 0 °C
9: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C
2: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
3: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
4: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
5: 97 percent / 1 h / -78 - 0 °C
6: 82 percent / diethyl ether / 0.5 h / 0 °C
7: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
2: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
3: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
4: 97 percent / 1 h / -78 - 0 °C
5: 82 percent / diethyl ether / 0.5 h / 0 °C
6: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 91 percent / KOt-Bu / dioxane / 2 h / 90 °C
2: 93 percent / 1 h / -78 - 0 °C
3: 93 percent / NaH / toluene; tetrahydrofuran / 1 h / 0 - 20 °C
4: 99 percent / DIBAl-H / diethyl ether / 3 h / 0 - 20 °C
5: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C
6: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
7: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
8: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
9: 97 percent / 1 h / -78 - 0 °C
10: 82 percent / diethyl ether / 0.5 h / 0 °C
11: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
2: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
3: 97 percent / 1 h / -78 - 0 °C
4: 82 percent / diethyl ether / 0.5 h / 0 °C
5: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
2: 97 percent / 1 h / -78 - 0 °C
3: 82 percent / diethyl ether / 0.5 h / 0 °C
4: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 99 percent / DIBAl-H / diethyl ether / 3 h / 0 - 20 °C
2: 96 percent / tBuOOH; Ti(OiPr)4; (-)-diethyl tartrate / CH2Cl2 / -40 - 20 °C
3: 96 percent / Red-Al / tetrahydrofuran / 1 h / 0 °C
4: 98 percent / imidazole / dimethylformamide / 44 h / 60 °C
5: 80 percent / H2 / Pd/C / ethanol / 48 h / 20 °C
6: 97 percent / 1 h / -78 - 0 °C
7: 82 percent / diethyl ether / 0.5 h / 0 °C
8: 80 percent / CrO3; H2SO4 / acetic acid / 2 h
View Scheme
参考文献
Kalesse, Markus; Quitschalle, Monika; Claus, Eckhard; Gerlach, Kai; Pahl, Axel; Meyer, Hartmut H.
European Journal of Organic Chemistry, 1999 , # 11 p. 2817 - 2823
反应条件
1: 0.046 g / triethylamine; DMAP / dimethylformamide / 1 h / 20 °C
2: 80 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 20 °C
View Scheme
参考文献
Jung, Jae-Chul; Kache, Rajashaker; Vines, Kimberly K.; Zheng, Yan-Song; Bijoy, Panicker; Valluri, Muralikrishna; Avery, Mitchell A.
Journal of Organic Chemistry, 2004 , vol. 69, # 26 p. 9269 - 9284
