(S)-5-羟甲基二氢呋喃-2-酮合成路线 （共 80 条）
反应条件
1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 3: tetrahydrofuran / -78 °C 4: DIBAL-H / toluene / 2 h / -78 °C 5: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 2 h, 2) 1,2-dichloroethane, a) 5 deg C, 10 min, b) room temperature, 10 min 7: 76 percent / 30percent aq. H2O2, pyridine / CH2Cl2 / 0.5 h / Ambient temperature 8: 78 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Kim; Misco
Tetrahedron Letters, 1992 , vol. 33, # 39 p. 5733 - 5736
反应条件
1.1: 86 percent / Et3N; DMAP / CH2Cl2 / 3 h / 0 - 20 °C 2.1: 95 percent / DIBAL / CH2Cl2 / 2 h / -78 °C 3.1: 77 percent / mesyl chloride; triethylamine / CH2Cl2 / 2.5 h / -20 - 40 °C 4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 - 0 °C 4.2: 85 percent / TMEDA / tetrahydrofuran / 12 h / 20 °C 5.1: ThxBH2 / tetrahydrofuran / 16 h / 0 °C 5.2: 59 percent / aq. NaOH; aq. H2O2 / 6 h / 20 °C 6.1: 93 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C 7.1: 74 percent / triphenylphosphine; iodine; imidazole / toluene / 3 h / 70 °C 8.1: 92 percent / ethanol / 3 h / Heating View Scheme
参考文献
Boukouvalas, John; Radu, Ioan-Iosif
Tetrahedron Letters, 2007 , vol. 48, # 17 p. 2971 - 2973
反应条件
1: 94 percent / pyridine, N,N-dimethylaminopyridine 2: 87 percent / sodium azide / 1 h / Heating 3: 67 percent / H2 / 5percent Pd/C / methanol / 2585.7 Torr View Scheme
参考文献
Herdeis
Synthesis, 1986 , vol. NO. 3, p. 232 - 233
反应条件
1: 94 percent / pyridine, N,N-dimethylaminopyridine 2: 87 percent / sodium azide / 1 h / Heating 3: 67 percent / H2 / 5percent Pd/C / methanol / 2585.7 Torr 4: 68 percent / diborane / tetrahydrofuran; hexane / 2 h / Heating View Scheme
参考文献
Olsen, Richard K.; Bhat, Krishna L.; Wardle, Robert B.; Hennen, William J.; Kini, Ganesh D.
Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 896 - 899
反应条件
1: 64 percent / pyridine / 20 h / Ambient temperature 2: 95 percent / KOH / methanol / 1 h / 60 °C 3: 80 percent / triphenylphosphine, diethyl azodicarboxylate / benzene; tetrahydrofuran / 24 h / Ambient temperature View Scheme
参考文献
Takano; Yonaga; Ogasawara
Synthesis, 1981 , vol. No.4, p. 265 - 266
反应条件
1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 3: tetrahydrofuran / -78 °C 4: DIBAL-H / toluene / 2 h / -78 °C 5: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 7: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 8: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 9: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Journal of Organic Chemistry, , vol. 57, # 14 p. 3887 - 3894
反应条件
pyridine in chloroform T=0°C; 12 h;
参考文献
Hanessian, Stephen; Giroux, Simon; Buffat, Maxime
Organic Letters, 2005 , vol. 7, # 18 p. 3989 - 3992
参考文献
Tomioka, Kiyoshi; Tanaka, Masahide; Koga, Kenji
Tetrahedron Letters, 1982 , vol. 23, # 33 p. 3401 - 3404
参考文献
Batmangherlich, Shari; Davidson, Alan H.
Journal of the Chemical Society, Chemical Communications, 1985 , # 20 p. 1399 - 1401
反应条件
4-(N,N-dimethlyamino)pyridine; triethylamine
参考文献
Paquette, Leo A.; Behrens, Garsten
Heterocycles, 1997 , vol. 46, # 1 p. 31 - 35
