2’,3’-二脱氧-3’-氟鸟苷合成路线 (共 28 条)
反应条件
2: NH3 / methanol / Ambient temperature
3: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature
4: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h
5: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
6: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
1: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
2: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
1: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature
2: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h
3: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
4: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
1: NaNO2 / acetic acid; H2O / Ambient temperature
2: 59 percent / NH3 / methanol / Ambient temperature
3: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature
4: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h
5: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
6: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
1: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h
2: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
3: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
2: pyridine / Ambient temperature
3: 86 percent / NH3 / methanol / Ambient temperature
4: NaNO2 / acetic acid; H2O / Ambient temperature
5: 59 percent / NH3 / methanol / Ambient temperature
6: 93 percent / lithium triethylborohydride / tetrahydrofuran; dimethylsulfoxide / Ambient temperature
7: 61 percent / Et3N, 4-dimethylaminopyridine / dimethylformamide / RT, 5 h; 4 deg C, 60 h
8: 35 percent / DAST / CH2Cl2 / 2 h / Ambient temperature
9: 72 percent / NH3 / methanol / Ambient temperature
View Scheme
参考文献
Herdewijn; Balzarini; Baba; Pauwels; Van Aerschot; Janssen; De Clerq
Journal of Medicinal Chemistry, 1988 , vol. 31, # 10 p. 2040 - 2048
反应条件
1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 18 h / 21 °C / Inert atmosphere
2: 2-hydroxyethanethiol; sodium hydroxide / water / 1.5 h / Inert atmosphere; Reflux; Large scale reaction
View Scheme
参考文献
Brodszki, Martin; Baeckstroem, Birthe; Malmgren, Hakan; Wennerberg, Johan; Larsson, Torbjoern; Pelcman, Mikael; Waehling, Horst; Wallberg, Hans; Horvath, Karol
Organic Process Research and Development, 2011 , vol. 15, # 5 p. 1027 - 1032
反应条件
1.1: H2SO4 / acetic acid / 2.5 h / 0 °C
2.1: aq. HCl / toluene; dioxane; cyclohexane / 8 h / 0 °C
3.1: o-H3PO4; nBu3N; 4 Angstroem molecular sieve / acetonitrile; various solvent(s) / 6 h / 0 °C
3.2: acetonitrile; various solvent(s)
4.1: KOH / H2O / 48 h / 50 °C
5.1: PNPase; CaCl2 / H2O / 5 h / 40 - 60 °C / Enzymatic reaction
View Scheme
参考文献
Komatsu, Hironori; Araki, Tadashi
Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2899 - 2901
反应条件
1.1: o-H3PO4; nBu3N; 4 Angstroem molecular sieve / acetonitrile; various solvent(s) / 6 h / 0 °C
1.2: acetonitrile; various solvent(s)
2.1: KOH / H2O / 48 h / 50 °C
3.1: PNPase; CaCl2 / H2O / 5 h / 40 - 60 °C / Enzymatic reaction
View Scheme
参考文献
Komatsu, Hironori; Araki, Tadashi
Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2899 - 2901
反应条件
1.1: aq. HCl / toluene; dioxane; cyclohexane / 8 h / 0 °C
2.1: o-H3PO4; nBu3N; 4 Angstroem molecular sieve / acetonitrile; various solvent(s) / 6 h / 0 °C
2.2: acetonitrile; various solvent(s)
3.1: KOH / H2O / 48 h / 50 °C
4.1: PNPase; CaCl2 / H2O / 5 h / 40 - 60 °C / Enzymatic reaction
View Scheme
参考文献
Komatsu, Hironori; Araki, Tadashi
Tetrahedron Letters, 2003 , vol. 44, # 14 p. 2899 - 2901