2-叠氮基-2-脱氧-D-吡喃葡萄糖1,3,4,6-四乙酸酯合成路线 （共 9 条）
反应条件
1: 90 percent / ZnI2 / 1,2-dichloro-ethane / 50 °C 2: 98 percent / NaOMe / methanol 3: 94 percent / pyridine 4: 100 percent / NaN3 / dimethylformamide / 80 °C 5: 86 percent / NaH / dimethylformamide 6: N-iodosuccinimide; silver trifluoromethanesulfonate / diethyl ether; CH2Cl2 / -20 °C 7: NaOMe / methanol 8: P(CH3)3; 0.1 N aq. NaOH / tetrahydrofuran 9: H2; aq. AcOH / 20 percent Pd(OH)2/C View Scheme
参考文献
Ryu, Do Hyun; Tan, Choon-Hong; Rando, Robert R.
Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 5 p. 901 - 903
反应条件
1.1: phosphoric acid / 2 h / 60 °C / Vacuum 2.1: sodium methylate / methanol / 1 h / 0 °C 3.1: hydrogen / methanol; water / 20 °C 4.1: methanol; water / 20 °C 4.2: 20 °C 5.1: Dithiothreitol; magnesium chloride / 3 h / 30 °C / pH 7 / aq. buffer; Enzymatic reaction View Scheme
参考文献
Masuko, Sayaka; Bera, Smritilekha; Green, Dixy E.; Weiwer, Michel; Liu, Jian; Deangelis, Paul L.; Linhardt, Robert J.
Journal of Organic Chemistry, 2012 , vol. 77, # 3 p. 1449 - 1456
反应条件
1: 92 percent / H2NNH2, AcOH / dimethylformamide / 0.03 h / 50 °C
2: LiN(TMS)2 / tetrahydrofuran / 1 h / 24 °C
View Scheme
参考文献
Shiozaki, Masao; Mochizuki, Takashi; Wakabayashi, Takanori; Kurakata, Shin-Ichi; Tatsuta, Tohru; Nishijima, Masahiro
Tetrahedron Letters, 1996 , vol. 37, # 40 p. 7271 - 7274
反应条件
1: 92 percent / H2NNH2, AcOH / dimethylformamide / 0.03 h / 50 °C
2: LiN(TMS)2 / tetrahydrofuran / 1 h / 24 °C
View Scheme
参考文献
Shiozaki, Masao; Mochizuki, Takashi; Wakabayashi, Takanori; Kurakata, Shin-Ichi; Tatsuta, Tohru; Nishijima, Masahiro
Tetrahedron Letters, 1996 , vol. 37, # 40 p. 7271 - 7274
反应条件
nitrogen; ammonia in tetrahydrofuran; methanol; dichloromethane
参考文献
Seeberger, Peter H.; Orgueira, Hernan; Schell, Peter
Patent: US2003/13862 A1, 2003 ;
反应条件
1: NH3 / tetrahydrofuran; methanol / 0.25 h
2: 29.8 g / imidazole / CH2Cl2 / 2 h
View Scheme
参考文献
Orgueira, Hernan A.; Bartolozzi, Alessandra; Schell, Peter; Litjens, Remy E. J. N.; Palmacci, Emma R.; Seeberger, Peter H.
Chemistry - A European Journal, 2003 , vol. 9, # 1 p. 140 - 169
反应条件
Multi-step reaction with 2 steps 1: triflic azide; DMAP / methanol / 18 h / 25 °C2: pyridine / 10 h / 0 °C
参考文献
Rele, Shyam M.; Iyer, Suri S.; Chaikof, Elliot L. Tetrahedron Letters, 2007 , vol. 48, # 29 p. 5055 - 5060
反应条件
Multi-step reaction with 2 steps 1: trifluoromethanesulfonyl azide2: pyridine
参考文献
Zhou, Jian; Matos, Marie-Christine; Murphy, Paul V. Organic Letters, 2011 , vol. 13, # 21 p. 5716 - 5719
反应条件
Multi-step reaction with 6 steps 1: NH3 / tetrahydrofuran; methanol / 0 °C2: imidazole / dimethylformamide / 20 h3: MeONa / methanol / 3 h4: NaH / dimethylformamide5: AcOH; ZnCl2 / 4 h / 20 °C6: Bu4NF; AcOH / tetrahydrofuran / 25 h
参考文献
La Ferla, Barbara; Luigi, Lay; Guerrini, Marco; Poletti, Laura; Panza, Luigi; Russo, Giovanni Tetrahedron, 1999 , vol. 55, # 32 p. 9867 - 9880
