(R)-(+)-1,2-环氧庚烷合成路线 （共 22 条）
反应条件
1: AD-mix-β / tert-butyl alcohol; water / 120 h / 0 °C
2: pyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 171 h / 0 - 20 °C / |Inert atmosphere
3: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / |Inert atmosphere
View Scheme
参考文献
Hale, Karl J.; Maczka, Maciej; Kaur, Amarjit; Manaviazar, Soraya; Ostovar, Mehrnoosh; Grabski, Milosz
Organic Letters, 2014 , vol. 16, # 4 p. 1168 - 1171
反应条件
1: 90 percent / pyridine, N,N-dimethyl-4-aminopyridine (DMAP) / CH2Cl2 / 4 h / Ambient temperature
2: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase
3: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h
View Scheme
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
反应条件
1: triethylamine / dichloromethane / 3 h / 25 °C / Inert atmosphere
2: potassium carbonate / methanol / 3 h / 25 °C
View Scheme
参考文献
Oliveira, Juliana M.; R. Freitas, Juliano C.; Comasseto, Joao Valdir; Menezes, Paulo Henrique
Tetrahedron, 2011 , vol. 67, # 16 p. 3003 - 3009
反应条件
1: aq. concd. HCl / methanol / 48 h / 20 °C
2: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min
View Scheme
参考文献
Hoeyer, Thomas; Kjaer, Anders; Lykkesfeldt, Jens
Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 5 p. 1042 - 1051
反应条件
1: 1.) Mg, 2.) Li2CuCl4 / 1.) ether, THF, 2.) THF, -78 to -55 deg C, 1 h
2: aq. concd. HCl / methanol / 48 h / 20 °C
3: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min
View Scheme
参考文献
Hoeyer, Thomas; Kjaer, Anders; Lykkesfeldt, Jens
Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 5 p. 1042 - 1051
反应条件
1: 1.) diisobutylaluminium hydride / 1.) n-hexane, toluene, 50 deg C, 4 h, 2.) + THF, room temperature, overnight
2: 75 percent / silver nitrate, silver oxide, 4 Angstroem molecular sieves / tetrahydrofuran / 9 h / 30 °C
3: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C
4: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C
View Scheme
参考文献
Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H.
Canadian Journal of Chemistry, 1993 , vol. 71, # 1 p. 60 - 67
反应条件
1: 75 percent / silver nitrate, silver oxide, 4 Angstroem molecular sieves / tetrahydrofuran / 9 h / 30 °C
2: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C
3: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C
View Scheme
参考文献
Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H.
Canadian Journal of Chemistry, 1993 , vol. 71, # 1 p. 60 - 67
反应条件
1: TBHP, Ti(O-i-Pr)4, diisopropyl L-tartrate, 4 Angstroem molecular sieves / CH2Cl2; 2,2,4-trimethyl-pentane / 44 h / -20 °C
2: tetraethylammonium fluoride hydrate / acetonitrile / 6 h / 60 °C
View Scheme
参考文献
Chan, T. H.; Chen, L. M.; Wang, D.; Li, L. H.
Canadian Journal of Chemistry, 1993 , vol. 71, # 1 p. 60 - 67
反应条件
sodium hydroxide; trimethyl-oxonium tetrafluoroborate
1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h; Yield given. Multistep reaction;
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
反应条件
1: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase
2: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h
View Scheme
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
