β-D-呋喃核糖-1,2,3,5-四乙酸酯合成路线 （共 86 条）
反应条件
N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate in 1,2-dichloro-ethane T=60°C; Vorbruggen nucleosidation reaction; 20 h; Inert atmosphere;
参考文献
Ellermann, Manuel; Paulini, Ralph; Jakob-Roetne, Roland; Lerner, Christian; Borroni, Edilio; Roth, Doris; Ehler, Andreas; Schweizer, W. Bernd; Schlatter, Daniel; Rudolph, Markus G.; Diederich, Francois
Chemistry - A European Journal, 2011 , vol. 17, # 23 p. 6369 - 6381
反应条件
1: 1.) SnCl4, 2.) EtONa / 1.) 1,2-dichloroethane, RT, 18 h, 2.) EtOH, RT, 1 h 2: 70 percent / 30percent NH4OH / 9 h / Ambient temperature View Scheme
参考文献
Franchetti, Palmarisa; Cappellacci, Loredana; Grifantini, Mario; Barzi, Anna; Nocentini, Giuseppe; et al.
Journal of Medicinal Chemistry, 1995 , vol. 38, # 19 p. 3829 - 3837
反应条件
1: 1,1,1,3,3,3-hexamethyl-disilazane; trimethylsilyl trifluoromethanesulfonate; 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide / acetonitrile / |Microwave irradiation 2: ammonia / methanol / 20 °C View Scheme
参考文献
Parmenopoulou, Vanessa; Chatzileontiadou, Demetra S.M.; Manta, Stella; Bougiatioti, Stamatina; Maragozidis, Panagiotis; Gkaragkouni, Dimitra-Niki; Kaffesaki, Eleni; Kantsadi, Anastassia L.; Skamnaki, Vassiliki T.; Zographos, Spyridon E.; Zounpoulakis, Panagiotis; Balatsos, Nikolaos A.A.; Komiotis, Dimitris; Leonidas, Demetres D.
Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 24 p. 7184 - 7193
反应条件
N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate in acetonitrile
Overall yield = < 28 percent;
参考文献
Ikeuchi, Kazutada; Fujii, Ryosuke; Sugiyama, Shimpei; Asakawa, Tomohiro; Inai, Makoto; Hamashima, Yoshitaka; Choi, Jae-Hoon; Suzuki, Tomohiro; Kawagishi, Hirokazu; Kan, Toshiyuki
Organic and Biomolecular Chemistry, 2014 , vol. 12, # 23 p. 3813 - 3815
反应条件
1.1: ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane / 4 h / Inert atmosphere; Reflux
1.2: 16 h / 20 °C
2.1: methanol; ammonia
View Scheme
参考文献
Battenberg, Oliver A.; Nodwell, Matthew B.; Sieber, Stephan A.
Journal of Organic Chemistry, 2011 , vol. 76, # 15 p. 6075 - 6087
反应条件
1: 4-nitro-1H-indazole With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane
20 h; Heating;
2: (2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate With trimethylsilyl trifluoromethanesulfonate in 1,2-dichloro-ethane
T=20°C; Hibert-Johnson glycosylation;
3: With ammonia in methanol
T=20°C; Title compound not separated from byproducts;
参考文献
Seela, Frank; Peng, Xiaohua
Nucleosides, Nucleotides and Nucleic Acids, 2004 , vol. 23, # 1-2 p. 227 - 237
反应条件
1: 1.) p-toluenesulfonic acid, 2.) ethanolic NH3 / 1.) a) RT, 10 min, b) 120 deg C, 15 min, 2.) 90 deg C, 16 h
2: 89 percent / m-chloroperoxybenzoic acid / ethanol / 19 h / Ambient temperature
3: 85 percent / NH3 / 48 h / Ambient temperature
View Scheme
参考文献
Montgomery, John A.; Shortnacy, Anita T.; Secrist, John A.
Journal of Medicinal Chemistry, 1983 , vol. 26, # 10 p. 1483 - 1489
反应条件
N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate in 1,2-dichloro-ethane
T=60°C; Vorbruggen nucleosidation reaction; 3 h; Inert atmosphere;
参考文献
Ellermann, Manuel; Paulini, Ralph; Jakob-Roetne, Roland; Lerner, Christian; Borroni, Edilio; Roth, Doris; Ehler, Andreas; Schweizer, W. Bernd; Schlatter, Daniel; Rudolph, Markus G.; Diederich, Francois
Chemistry - A European Journal, 2011 , vol. 17, # 23 p. 6369 - 6381
反应条件
methanol; ammonium sulfate; ammonia; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane
Yield given. Multistep reaction;
参考文献
Patil, Vemanna D.; Wise, Dean S.; Townsend, Leroy B.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1853 - 1858
反应条件
ammonium hydroxide; tin(IV) chloride
1.) CH3CN, 1 h, reflux, 2.) MeOH, 12 h; Yield given. Multistep reaction;
参考文献
Schlimme, Eckhard
Liebigs Annalen der Chemie, 1981 , # 10 p. 1903 - 1906
