(3aR,4S,5R,6aS)-4-[[[(1,1-二甲基乙基)二甲基硅基]氧基]甲基]六氢-5-[(四氢-2H-吡喃-2-基)氧基]-2H-环戊并[b]呋喃-2-酮合成路线 （共 18 条）
反应条件
1: 65 percent / CH3ONa / methanol / 1.33 h / Ambient temperature 2: 90 percent / PPTS / 1,2-dichloro-ethane / 2 h / Ambient temperature View Scheme
参考文献
Collection of Czechoslovak Chemical Communications, , vol. 62, # 8 p. 1325 - 1341
反应条件
1.1: sulfuric acid / 24 h / 50 - 80 °C / |Sealed tube 2.1: DBN / methanol / 12 h / 20 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / |Inert atmosphere 3.2: 8 h / |Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / |Inert atmosphere View Scheme
参考文献
Tetrahedron Letters, , vol. 54, # 21 p. 2726 - 2728
反应条件
1.1: DBN / methanol / 12 h / 20 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / |Inert atmosphere 2.2: 8 h / |Inert atmosphere 3.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / |Inert atmosphere View Scheme
参考文献
Tetrahedron Letters, , vol. 54, # 21 p. 2726 - 2728
反应条件
3,4-dihydro-2H-pyran; toluene-4-sulfonic acid Yield given;
参考文献
Terinek, Miroslav; Kozmik, Vaclav; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1997 , vol. 62, # 8 p. 1325 - 1341
反应条件
toluene-4-sulfonic acid Yields of byproduct given;
参考文献
Terinek, Miroslav; Kozmik, Vaclav; Palecek, Jaroslav
Collection of Czechoslovak Chemical Communications, 1997 , vol. 62, # 8 p. 1325 - 1341
反应条件
tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 18 h; Inert atmosphere;
参考文献
SUCAMPO AG; UENO, Ryuji
Patent: WO2013/22079 A1, 2013 ;
Location in patent: Page/Page column 37-39 ;
反应条件
1: DIBAH / toluene / -78 °C
2: toluene / 60 °C
3: H2 / 10percent Pd/C / methanol / Ambient temperature
4: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
5: Zn, TiCl4 / Ambient temperature
6: 100 percent / Siam2BH / tetrahydrofuran / 0 °C
7: LiAlH4 / tetrahydrofuran / 0 °C
8: (COCl)2, DMSO, Et3N / CH2Cl2 / -78 °C
9: (PhCH2)2NH2(+)*TFA(-) / benzene / 60 °C
10: tBuOK / tetrahydrofuran / Ambient temperature
11: 9-BBN / tetrahydrofuran / 0 °C
12: 50percent aq. NaOH / Bu4N*HSO4 / CH2Cl2 / 40 °C
13: Bu4NF / tetrahydrofuran / Ambient temperature
14: SO3*Py, Et3N / dimethylsulfoxide / Ambient temperature
15: 90 percent / NaH / tetrahydrofuran / Ambient temperature
16: 100 percent / AcOH / tetrahydrofuran; H2O / 50 °C
17: 79 percent / diisobutylaluminum 2,6-di-t-butyl-4-methylphenoxide / toluene / -78 - -20 °C
18: 90 percent / 7percent aq. KOH / methanol
View Scheme
参考文献
Shibasaki; Takahashi; Aoki; Sato; Narita
Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 6 p. 1647 - 1649
反应条件
dimethylaluminum chloride in dichloromethane
T=-25 - 25°C; 1 h;
参考文献
Ogawa, Yugi; Shibasaki, Masakatsu
Tetrahedron Letters, 1984 , vol. 25, # 6 p. 663 - 664
