(-)-5-羟基-3-[[2-羟基-1-(羟基甲基)乙基]氨基]-5-(羟基甲基)-2-甲氧基-2-环己烯-1-酮合成路线 （共 10 条）
反应条件
1: 76 percent / N-bromosuccinimide / CCl4 / 1.3 h
2: 1.) NaBH4, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h
3: 64 percent / PCC / CH2Cl2 / 11 h / Heating
4: 88 percent / dimethylformamide / 15 h / 25 °C
5: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
6: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
7: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
8: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
9: 94 percent / diethyl ether / 3 h / 25 °C
10: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
11: NaBH4 / methanol; H2O / 3 h / 0 °C
12: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 97 percent / p-TsOH / benzene / 19 h / Heating
2: 76 percent / N-bromosuccinimide / CCl4 / 1.3 h
3: 1.) NaBH4, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h
4: 64 percent / PCC / CH2Cl2 / 11 h / Heating
5: 88 percent / dimethylformamide / 15 h / 25 °C
6: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
7: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
8: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
9: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
10: 94 percent / diethyl ether / 3 h / 25 °C
11: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
12: NaBH4 / methanol; H2O / 3 h / 0 °C
13: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 1.) NaBH4, 2.) p-TsOH / 1.) i-PrOH, 2.) acetone, reflux, 2 h
2: 64 percent / PCC / CH2Cl2 / 11 h / Heating
3: 88 percent / dimethylformamide / 15 h / 25 °C
4: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
5: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
6: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
7: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
8: 94 percent / diethyl ether / 3 h / 25 °C
9: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
10: NaBH4 / methanol; H2O / 3 h / 0 °C
11: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 49 percent / NH4Cl, NH4OH / propan-2-ol / 15 h / 25 °C
2: 64 percent / PCC / CH2Cl2 / 11 h / Heating
3: 88 percent / dimethylformamide / 15 h / 25 °C
4: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
5: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
6: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
7: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
8: 94 percent / diethyl ether / 3 h / 25 °C
9: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
10: NaBH4 / methanol; H2O / 3 h / 0 °C
11: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 64 percent / PCC / CH2Cl2 / 11 h / Heating
2: 88 percent / dimethylformamide / 15 h / 25 °C
3: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
4: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
5: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
6: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
7: 94 percent / diethyl ether / 3 h / 25 °C
8: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
9: NaBH4 / methanol; H2O / 3 h / 0 °C
10: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 88 percent / dimethylformamide / 15 h / 25 °C
2: 99 percent / diethyl ether; ethyl acetate / 15 h / 0 °C
3: 62 percent / (i-Bu)2AlH / CH2Cl2 / 3 h / 0 °C
4: PCC, NaOAc / CH2Cl2 / 13 h / 25 °C
5: NaN3 / LiCl / dimethylformamide / 15 h / 25 °C
6: 94 percent / diethyl ether / 3 h / 25 °C
7: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
8: NaBH4 / methanol; H2O / 3 h / 0 °C
9: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
trifluoroacetic acid
T=0°C; 0.333333 h; Yield given;
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 94 percent / diethyl ether / 3 h / 25 °C
2: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
3: NaBH4 / methanol; H2O / 3 h / 0 °C
4: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: NaBH4 / methanol; H2O / 3 h / 0 °C
2: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
反应条件
1: 2.) NaBH3CN / 1.) Et2O, reflux, 2 h, 2.) MeOH, 25 deg C, 1 h
2: NaBH4 / methanol; H2O / 3 h / 0 °C
3: 50percent aq. TFA / 0.33 h / 0 °C
View Scheme
参考文献
White; Cammack; Sakuma
Journal of the American Chemical Society, 1989 , vol. 111, # 24 p. 8970 - 8972
