(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇合成路线 （共 14 条）
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
sodium methylate in methanol 48 h; Heating;
参考文献
Lichtenthaler, Frieder W.; Klaeres, Ulrich; Szurmai, Zoltan; Werner, Bernd
Carbohydrate Research, 1997 , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 1.) NaH, tetrabutylammonium iodide / 1.) THF, 0 deg C -> room temperature, 2.) THF, 50 deg C, 2 h 2: 81 percent / Dowex 50 (H(1+)) / H2O / 2 h / 70 °C 3: 23.2 g / pyridine / CHCl3 / 24 h / Ambient temperature 4: hydrogen bromide, acetic acid / CH2Cl2 / 0.17 h 5: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 1.5 h / Ambient temperature 6: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 7: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 8: 89 percent / pyridine / 1 h 9: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 10: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 11: 53 percent / pyridine / 8 h / Ambient temperature 12: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 13: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 14: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 81 percent / Dowex 50 (H(1+)) / H2O / 2 h / 70 °C 2: 23.2 g / pyridine / CHCl3 / 24 h / Ambient temperature 3: hydrogen bromide, acetic acid / CH2Cl2 / 0.17 h 4: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 1.5 h / Ambient temperature 5: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 6: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 7: 89 percent / pyridine / 1 h 8: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 9: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 10: 53 percent / pyridine / 8 h / Ambient temperature 11: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 12: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 13: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 23.2 g / pyridine / CHCl3 / 24 h / Ambient temperature 2: hydrogen bromide, acetic acid / CH2Cl2 / 0.17 h 3: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 1.5 h / Ambient temperature 4: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 5: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 6: 89 percent / pyridine / 1 h 7: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 8: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 9: 53 percent / pyridine / 8 h / Ambient temperature 10: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 11: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 12: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 1.5 h / Ambient temperature 2: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 3: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 4: 89 percent / pyridine / 1 h 5: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 6: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 7: 53 percent / pyridine / 8 h / Ambient temperature 8: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 9: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 10: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: hydrogen bromide, acetic acid / CH2Cl2 / 0.17 h 2: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH2Cl2 / 1.5 h / Ambient temperature 3: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 4: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 5: 89 percent / pyridine / 1 h 6: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 7: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 8: 53 percent / pyridine / 8 h / Ambient temperature 9: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 10: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 11: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 2: 89 percent / pyridine / 1 h 3: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 4: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 5: 53 percent / pyridine / 8 h / Ambient temperature 6: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 7: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 8: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 2: 53 percent / pyridine / 8 h / Ambient temperature 3: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 4: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 5: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH2Cl2 / 0.5 h 2: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH2Cl2, 15 min, 2.) dioxane, water, 20 min 3: 89 percent / pyridine / 1 h 4: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 5: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 6: 53 percent / pyridine / 8 h / Ambient temperature 7: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 8: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 9: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
→
140147-36-0(2R,3S,4S,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-二羟基-2-辛氧基-6-[[(2S,3S,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基甲基]四氢吡喃-4-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇
反应条件
1: 89 percent / pyridine / 1 h 2: 96 percent / NaOMe / methanol; CH2Cl2 / 4.5 h 3: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH2Cl2, 15 min, 2.) CH2Cl2, room temperature, 24 h 4: 53 percent / pyridine / 8 h / Ambient temperature 5: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature 6: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH2Cl2, room temperature, 30 min, 2.) CH2Cl2, room temperature, 45 min 7: 84 percent / sodium methoxide / methanol / 48 h / Heating View Scheme
参考文献
Carbohydrate Research, , vol. 305, # 2 p. 293 - 303
