Clasto-lactacystin (Omuralide)合成路线 （共 96 条）
反应条件
1: aq. NaOH / 10 h / 20 °C 2: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: 99 percent / HF / acetonitrile / 7 h / 20 °C 2: H2CrO4 / acetone / 6 h / 0 - 20 °C 3: aq. NaOH / 10 h / 20 °C 4: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: pyridine / 3 h / 20 °C 2: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 3: 99 percent / HF / acetonitrile / 7 h / 20 °C 4: H2CrO4 / acetone / 6 h / 0 - 20 °C 5: aq. NaOH / 10 h / 20 °C 6: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: PDC; Celite / dimethylformamide / 52 h / 20 °C 2: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C 3: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 4: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 5: pyridine / 3 h / 20 °C 6: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 7: 99 percent / HF / acetonitrile / 7 h / 20 °C 8: H2CrO4 / acetone / 6 h / 0 - 20 °C 9: aq. NaOH / 10 h / 20 °C 10: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: p-TsOH*H2O / acetone / 25 h / 20 °C 2: PDC; Celite / dimethylformamide / 52 h / 20 °C 3: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C 4: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 5: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 6: pyridine / 3 h / 20 °C 7: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 8: 99 percent / HF / acetonitrile / 7 h / 20 °C 9: H2CrO4 / acetone / 6 h / 0 - 20 °C 10: aq. NaOH / 10 h / 20 °C 11: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: 1.11 g / tetrahydrofuran; diethyl ether / 0 °C 2: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 3: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 4: pyridine / 3 h / 20 °C 5: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 6: 99 percent / HF / acetonitrile / 7 h / 20 °C 7: H2CrO4 / acetone / 6 h / 0 - 20 °C 8: aq. NaOH / 10 h / 20 °C 9: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: 97 percent Turnov. / diethyl ether / 20 h / 20 °C 2: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 3: pyridine / 3 h / 20 °C 4: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 5: 99 percent / HF / acetonitrile / 7 h / 20 °C 6: H2CrO4 / acetone / 6 h / 0 - 20 °C 7: aq. NaOH / 10 h / 20 °C 8: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: 100 percent / p-TsOH*H2O / methanol / 24 h / 60 °C 2: pyridine / 3 h / 20 °C 3: 165 mg / pyridine; 4-(dimethylamino)pyridine / 27 h / 20 °C 4: 99 percent / HF / acetonitrile / 7 h / 20 °C 5: H2CrO4 / acetone / 6 h / 0 - 20 °C 6: aq. NaOH / 10 h / 20 °C 7: 96 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 22 p. 7765 - 7768
反应条件
1: MnO2; 4 Angstroem molecular sieves / CH2Cl2 / Heating 2: NaCNBH3; AcOH / methanol / 0 °C 3: 83 percent / KHMDS / tetrahydrofuran; toluene / 6 h / -30 °C 4: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 5: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 6: NaBH4 / methanol / 20 °C 7: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 8: 100 percent / tetrahydrofuran / Heating 9: n-Bu3SnH; AIBN / toluene / Heating 10: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 11: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 12: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 13: 74 percent / NaOMe / methanol / 20 °C 14: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
反应条件
1: 93 percent / TPAP; 4-Angstroem molecular sieves; NMO / acetonitrile 2: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 °C 3: NaBH4 / methanol / 20 °C 4: 96 percent / K2OsO2(OH)4; aq. citric acid; NMO / 2-methyl-propan-2-ol / 20 °C 5: 100 percent / tetrahydrofuran / Heating 6: n-Bu3SnH; AIBN / toluene / Heating 7: 90 percent / dimethyldioxirane / acetone / 18 h / 0 - 3 °C 8: 35 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C 9: 95 percent / aq. NaClO2; NaH2PO4; HOSO2NH2 / 2-methyl-propan-2-ol / 20 °C 10: 74 percent / NaOMe / methanol / 20 °C 11: 45 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; Et3N / CH2Cl2 / 20 °C View Scheme
参考文献
Organic and Biomolecular Chemistry, , vol. 4, # 2 p. 193 - 195
