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
trimethylsilylazide in tert-butyl alcohol 10 h; Inert atmosphereReflux;
参考文献
CATABASIS PHARMACEUTICALS, INC.; MILNE, Jill C.; JIROUSEK, Michael R.; VU, Chi B.; WENSLEY, Allison; TING, Amal
Patent: WO2013/90420 A2, 2013 ;
Location in patent: Paragraph 00176 ;
反应条件
1: With trimethylsilylazide in tert-butyl alcohol Inert atmosphereReflux; 2: With hydrogenchloride; sodium nitrite in water; tert-butyl alcohol 1 h;
参考文献
TSRL, INC.; HILFINGER, John; SHEN, Wei
Patent: WO2011/123856 A1, 2011 ;
Location in patent: Page/Page column 42 ;
WO 2011/123856 A1
反应条件
1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=10°C; 1 h;
参考文献
Liu, Ke-Gang; Yan, Shi; Wu, Yu-Lin; Yao, Zhu-Jun
Organic Letters, 2004 , vol. 6, # 13 p. 2269 - 2272
反应条件
diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene 23 h; Ambient temperature;
参考文献
Scheigetz, John; Zamboni, Robert; Bernstein, Michael A.; Roy, Bruno
Organic Preparations and Procedures International, 1995 , vol. 27, # 6 p. 637 - 644
反应条件
1: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 3: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 4: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 5: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 6: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 7: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 8: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 9: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 10: 65 percent / pyridine / 12 h / 20 °C 11: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 12: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
反应条件
1: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 2: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 3: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 4: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 5: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 6: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 7: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 8: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 9: 65 percent / pyridine / 12 h / 20 °C 10: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 11: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
反应条件
1: 88 percent / Et3N / CH2Cl2 2: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C 3: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 4: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 5: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 6: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 7: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 8: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 9: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 10: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 11: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 12: 65 percent / pyridine / 12 h / 20 °C 13: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 14: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
反应条件
1: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C 2: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 3: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 4: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 5: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 6: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 7: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 8: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 9: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 10: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 11: 65 percent / pyridine / 12 h / 20 °C 12: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 13: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
反应条件
1: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 2: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 3: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 4: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 5: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 6: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 7: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 8: 65 percent / pyridine / 12 h / 20 °C 9: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 10: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
反应条件
1: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 2: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 3: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 4: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 6: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 7: 65 percent / pyridine / 12 h / 20 °C 8: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 9: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme
参考文献
Organic Letters, , vol. 6, # 13 p. 2269 - 2272
