(3R,3AS,6AR)-六氢呋喃并[2,3-B]呋喃-3-醇合成路线 （共 53 条）
反应条件
hydrogenchloride; water in tetrahydrofuran T=20°C; 44 h; Product distribution / selectivity;
参考文献
WO2008/34598 A1, ;
Page/Page column 23-24 ;
反应条件
hydrogenchloride; water in tetrahydrofuran T=0 - 4°C; 18 h; Product distribution / selectivity;
参考文献
WO2008/34598 A1, ;
Page/Page column 24-25 ;
反应条件
1.1: water; sodium sulfite / dichloromethane 2.1: ethanol; sodium tetrahydroborate / 8 h / 15 - 60 °C / Inert atmosphere 2.2: 3 h / -10 - 0 °C 3.1: triethylamine / N,N-dimethylaminopyridine 4.1: sodium hydrogencarbonate; water; sodium dihydrogen phosphate dihydrate; CAL-B enzyme / 40 - 45 °C / Enzymatic reaction 5.1: potassium carbonate; methanol / 25 - 35 °C View Scheme
反应条件
1.1: lithium borohydride / tetrahydrofuran / 10 h / 65 - 70 °C / Inert atmosphere 1.2: 2 h / -10 - 0 °C 2.1: triethylamine / N,N-dimethylaminopyridine 3.1: sodium hydrogencarbonate; water; sodium dihydrogen phosphate dihydrate; CAL-B enzyme / 40 - 45 °C / Enzymatic reaction 4.1: potassium carbonate; methanol / 25 - 35 °C View Scheme
反应条件
1.1: triethylamine; hydrogen / 5 palladium on charcoal / ethanol / 8 h 2.1: lithium borohydride / tetrahydrofuran / 10 h / 65 - 70 °C / Inert atmosphere 2.2: 2 h / -10 - 0 °C 3.1: triethylamine / N,N-dimethylaminopyridine 4.1: sodium hydrogencarbonate; water; sodium dihydrogen phosphate dihydrate; CAL-B enzyme / 40 - 45 °C / Enzymatic reaction 5.1: potassium carbonate; methanol / 25 - 35 °C View Scheme
反应条件
1: p-TsOH*H2O / 3 h / 24 °C 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -50 deg C to -20 deg C, 1.5 h, 2.) CH2Cl2, from -20 deg C to RT, 1 h 3: 815 mg / camphorsulfonic acid / 12 h / 24 °C 4: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 1 h, 2.) MeOH, CH2Cl2, from -78 deg C to RT 5: 430 mg / NaBH4 / ethanol / 0.25 h / 0 °C 6: 350 mg / camphorsulfonic acid / CH2Cl2 / 12 h / 23 °C View Scheme
参考文献
Journal of medicinal chemistry, , vol. 39, # 17 p. 3278 - 3290
反应条件
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -50 deg C to -20 deg C, 1.5 h, 2.) CH2Cl2, from -20 deg C to RT, 1 h 2: 815 mg / camphorsulfonic acid / 12 h / 24 °C 3: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 1 h, 2.) MeOH, CH2Cl2, from -78 deg C to RT 4: 430 mg / NaBH4 / ethanol / 0.25 h / 0 °C 5: 350 mg / camphorsulfonic acid / CH2Cl2 / 12 h / 23 °C View Scheme
参考文献
Journal of medicinal chemistry, , vol. 39, # 17 p. 3278 - 3290
反应条件
1: 430 mg / NaBH4 / ethanol / 0.25 h / 0 °C 2: 350 mg / camphorsulfonic acid / CH2Cl2 / 12 h / 23 °C View Scheme
参考文献
Journal of medicinal chemistry, , vol. 39, # 17 p. 3278 - 3290
反应条件
1: LiAlH4 / diethyl ether / 1.) RT, 12 h, 2.) reflux, 1 h 2: p-TsOH*H2O / 3 h / 24 °C 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, from -50 deg C to -20 deg C, 1.5 h, 2.) CH2Cl2, from -20 deg C to RT, 1 h 4: 815 mg / camphorsulfonic acid / 12 h / 24 °C 5: 1.) O3, 2.) Me2S / 1.) MeOH, CH2Cl2, -78 deg C, 1 h, 2.) MeOH, CH2Cl2, from -78 deg C to RT 6: 430 mg / NaBH4 / ethanol / 0.25 h / 0 °C 7: 350 mg / camphorsulfonic acid / CH2Cl2 / 12 h / 23 °C View Scheme
参考文献
Journal of medicinal chemistry, , vol. 39, # 17 p. 3278 - 3290
反应条件
tin(II) trifluoromethanesulfonate in dichloromethane T=0 - 20°C; optical yield given as percent eeenantioselective reaction;
参考文献
Organic Letters, , vol. 10, # 6 p. 1103 - 1106
