5-乙酰氨基-7,8,9-O-三乙酰基-2,6-脱水-4-叠氮-3,4,5-三脱氧-D-甘油-D-半乳-2-壬烯酸甲酯合成路线 （共 44 条）
反应条件
1: boron trifluoride diethyl etherate / acetone / 1 h / 0 °C / Inert atmosphere 2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 3: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 6: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 7: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 8: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 9: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 10: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 11: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 12: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 13: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 14: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 15: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 16: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 17: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 18: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 19: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 5: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 6: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 7: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 8: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 9: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 10: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 11: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 12: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 13: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 14: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 15: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 16: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 17: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 18: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-tartaric acid diethyl ester / decane; dichloromethane / 69 h / -20 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 4: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 5: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 6: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 7: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 8: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 9: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 10: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 11: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 12: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 13: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 14: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 15: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 16: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 17: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: tetrabutyl ammonium fluoride; water / acetonitrile / 91 h / 50 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 4: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 5: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 6: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 7: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 8: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 9: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 10: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 11: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 12: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 13: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 14: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 15: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 16: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 3: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 4: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 6: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 7: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 9: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 10: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 11: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 12: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 13: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 14: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 15: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: hydrogenchloride / 1,4-dioxane; dichloromethane / 3 h / 0 °C / Inert atmosphere 2: triethylamine / ethyl acetate / 0.17 h / 0 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 5: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 6: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 7: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 8: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 9: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 10: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 11: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 12: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 13: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 14: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: 2,6-dimethylpyridine / dichloromethane / 0.58 h / -78 - 20 °C / Inert atmosphere 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 2.5 h / 45 °C / Inert atmosphere 3: sodium periodate / water; acetone; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere 4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere 5: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 6: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C / Inert atmosphere 7: 30 Pd/C; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C / 760.05 Torr / Inert atmosphere 8: pyridine; 4-(N,N-dimethlyamino)pyridine / 5.5 h / 20 °C / Inert atmosphere 9: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 10: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 11: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 12: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 2: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 3: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: triphenylphosphine hydrobromide / acetonitrile / 5 h / 0 - 55 °C / Inert atmosphere 2: copper(I) bromide / dichloromethane / 3 h / Reflux; Inert atmosphere 3: sulfuric acid; acetic acid / 12 h / 0 - 20 °C / Inert atmosphere 4: trimethylsilylazide / tert-butyl alcohol / 10 h / Reflux; Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 7 p. 1644 - 1647
反应条件
1: 78 percent / H2S, pyridine / 1.5 h / Ambient temperature 2: diisopropylethylamine / dimethylformamide / 96 h / Ambient temperature 3: aq. NaOH / methanol / Ambient temperature View Scheme
参考文献
Nitabaru, Tatsuya; Kumagai, Naoya; Shibasaki, Masakatsu
Angewandte Chemie - International Edition, 2012 , vol. 51, # 7 p. 1644 - 1647
