(S)-5-羟甲基二氢呋喃-2-酮合成路线 （共 80 条）
反应条件
1: 46 percent / imidazole 2: 92 percent / DIBAL / 0.08 h / -78 °C 3: CCl4, tris(dimethylamino)phosphane / tetrahydrofuran / 4 h / -80 °C 4: 20 percent / KOH, tris<2-(2-methoxyethoxy)ethyl>amine / acetonitrile / 0.5 h / Ambient temperature 5: 82 percent / Bu4NF / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme
参考文献
Seela, Frank; Muth, Heinz-Peter; Roeling, Angelika
Helvetica Chimica Acta, 1991 , vol. 74, # 3 p. 554 - 564
反应条件
1: 42 percent / pyridine / a) r.t., 0.5h, b) 80 deg C, 3h 2: DIBAL / tetrahydrofuran; hexane / 0.5 h / -75 °C 3: 0.2 percent HCl / 0.25 h / Ambient temperature 4: trimethylsilyl triflate / CH2Cl2 / Ambient temperature 5: 39 percent / conc.NH3 / methanol / Ambient temperature View Scheme
参考文献
Abdel-Megied, Ahmed E.-S.; Pedersen, Erik B.; Nielsen, Carsten M.
Monatshefte fuer Chemie, 1991 , vol. 122, # 1.2 p. 59 - 70
反应条件
1: 42 percent / pyridine / a) r.t., 0.5h, b) 80 deg C, 3h 2: DIBAL / tetrahydrofuran; hexane / 0.5 h / -75 °C 3: 0.2 percent HCl / 0.25 h / Ambient temperature 4: trimethylsilyl triflate / CH2Cl2 / Ambient temperature View Scheme
参考文献
Abdel-Megied, Ahmed E.-S.; Pedersen, Erik B.; Nielsen, Carsten M.
Monatshefte fuer Chemie, 1991 , vol. 122, # 1.2 p. 59 - 70
反应条件
1: 88 percent / (C2H5)3N / CH2Cl2 / 1.) -30 deg C, 5 min, 2.) room temp., 2 h 2: 93 percent / NaN3, 18-crown-6 / acetonitrile / 12 h / Heating 3: H2 / Pd/C / methanol / 3 h / 30 °C / 2250.2 Torr 4: aq. Ba(OH)2 / 12 h / Heating View Scheme
参考文献
Herdeis
Synthesis, 1986 , vol. NO. 3, p. 232 - 233
反应条件
1: 88 percent / (C2H5)3N / CH2Cl2 / 1.) -30 deg C, 5 min, 2.) room temp., 2 h 2: 93 percent / NaN3, 18-crown-6 / acetonitrile / 12 h / Heating 3: H2 / Pd/C / methanol / 3 h / 30 °C / 2250.2 Torr View Scheme
参考文献
Herdeis
Synthesis, 1986 , vol. NO. 3, p. 232 - 233
反应条件
1: 90 percent / imidazole / CH2Cl2 / 3 h 2: DIBAL-H / CH2Cl2; toluene / 2 h / -90 °C 3: molecular sieves (4 Angstroem), BF3*OEt2 / diethyl ether / 0.5 h 4: 1.) 1,1,1,3,3,3-heksamethylenedisilazane, ammonium sulfate, 2.) SnCl4, TMSOTf / 1.) reflux, 2 h, 2.) 1,2-dichloroethane, RT, 2 h 5: TBAF / tetrahydrofuran / 8 h / Ambient temperature View Scheme
参考文献
Beach, J. Warren; Kim, Hea O.; Jeong, Lak S.; Nampalli, Satyanarayana; Islam, Qamrul; et al.
Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3887 - 3894
反应条件
1: 90 percent / imidazole / CH2Cl2 / 3 h 2: DIBAL-H / CH2Cl2; toluene / 2 h / -90 °C 3: molecular sieves (4 Angstroem), BF3*OEt2 / diethyl ether / 0.5 h 4: 1.) 1,1,1,3,3,3,-hexamethyldisilazane, ammonium sulfate, 2.) SnCl4, TMSOTf / 1.) reflux, 2 h, 2.) 1,2-dichloroethane, RT, 2 h 5: TBAF / tetrahydrofuran / 8 h / Ambient temperature View Scheme
参考文献
Beach, J. Warren; Kim, Hea O.; Jeong, Lak S.; Nampalli, Satyanarayana; Islam, Qamrul; et al.
Journal of Organic Chemistry, 1992 , vol. 57, # 14 p. 3887 - 3894
反应条件
1: 96 percent / imidazole / CH2Cl2 / 4 h / 0 - 20 °C 2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h 3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature 4: 96 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / 0 °C 5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h 6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h 7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C 8: 92 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et3N / dimethylformamide / 18 h / 0 - 20 °C 9: 69 percent / 8N HCl / propan-2-ol / 6 h / Ambient temperature View Scheme
参考文献
Dorsey; Levin; McDaniel; Vacca; Guare; Darke; Zugay; Emini; Schleif; Quintero; Lin; Chen -; Holloway; Fitzgerald; Axel; Ostovic; Anderson; Huff
Journal of Medicinal Chemistry, 1994 , vol. 37, # 21 p. 3443 - 3451
反应条件
1: pyridine / 4 h / 50 °C 2: DIBAL-H / tetrahydrofuran / 2 h / -78 °C 3: thionyl chloride / CH2Cl2 / 2 h / 23 °C 4: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 5: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 6: DBU / CH2Cl2 / 1 h / 0 °C 7: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme
参考文献
Kim; Misco
Tetrahedron Letters, 1992 , vol. 33, # 39 p. 5733 - 5736
反应条件
1: 42 percent / pyridine / a) r.t., 0.5h, b) 80 deg C, 3h 2: DIBAL / tetrahydrofuran; hexane / 0.5 h / -75 °C 3: 0.2 percent HCl / 0.25 h / Ambient temperature 4: trimethylsilyl triflate / CH2Cl2 / Ambient temperature 5: 89 percent / POCl3, Et3N / acetonitrile / Ambient temperature 6: 20percent aq.NH3 / dioxane / Ambient temperature 7: 21 percent / methanolic ammonia / Ambient temperature View Scheme
参考文献
Abdel-Megied, Ahmed E.-S.; Pedersen, Erik B.; Nielsen, Carsten M.
Monatshefte fuer Chemie, 1991 , vol. 122, # 1.2 p. 59 - 70
