[(1R,2R,4R,5R)-2-(6-氨基嘌呤-9-基)-3,6-二氧杂双环[3.1.0]己烷-4-基]甲醇合成路线 （共 7 条）
反应条件
1: 100 percent / pyridine / 12 h / 20 °C 2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C 3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C 4: NaH / tetrahydrofuran / 12 h / -20 °C 5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 6: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 7: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 8: pyridine / 48 h / 5 °C 9: 59.4 mg / TMSCl / pyridine 10: 25.8 mg / pyridine; H2O / 19 h / 20 °C 11: 62 percent / DCC; N-hydroxysuccinimide / dimethylformamide / 0 - 20 °C 12: 36 percent / TFA / 0.13 h / 20 °C View Scheme
参考文献
Robins, Morris J.; Miles, Robert W.; Samano, Mirna C.; Kaspar, Roger L.
Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8204 - 8210
反应条件
1: 100 percent / pyridine / 12 h / 20 °C 2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C 3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C 4: NaH / tetrahydrofuran / 12 h / -20 °C 5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C 6: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C 7: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating 8: pyridine / 48 h / 5 °C 9: 59.4 mg / TMSCl / pyridine 10: 25.8 mg / pyridine; H2O / 19 h / 20 °C View Scheme
参考文献
Robins, Morris J.; Miles, Robert W.; Samano, Mirna C.; Kaspar, Roger L.
Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8204 - 8210
反应条件
lithium triethylborohydride in tetrahydrofuran; dimethyl sulfoxide 1.) 4 deg C, 1 h, 2.) 19-22 deg C, overnight;
参考文献
Robins, Morris J.; Wilson, John, S.; Madej, Danuta; Low, Nicholas H.; Hansske, Fritz; Wnuk, Stanislaw F.
Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7902 - 7908
反应条件
1: 100 percent / pyridine / 12 h / 20 °C
2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C
3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C
4: NaH / tetrahydrofuran / 12 h / -20 °C
5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C
6: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C
7: 92 percent / NH4HCO2 / Pd(OH)2-C / H2O; methanol / 1.5 h / Heating
View Scheme
参考文献
Schirmeister-Tichy, Helga; Iacono, Kathryn T.; Muto, Nicholas F.; Homan, Joseph W.; Suhadolnik, Robert J.; Pfleiderer, Wolfgang
Helvetica Chimica Acta, 1999 , vol. 82, # 4 p. 597 - 613
反应条件
Multi-step reaction with 2 steps 1: lithium triethylborohydride / dimethyl sulfoxide2: mammalian adenosine deaminase / |Enzymatic reaction
参考文献
Vodnala, Suman K.; Lundbaeck, Thomas; Yeheskieli, Esther; Sjoeberg, Birger; Gustavsson, Anna-Lena; Svensson, Richard; Olivera, Gabriela C.; Eze, Anthonius A.; De Koning, Harry P.; Hammarstroem, Lars G. J.; Rottenberg, Martin E. Journal of Medicinal Chemistry, 2013 , vol. 56, # 24 p. 9861 - 9873
反应条件
Multi-step reaction with 6 steps 1: 100 percent / pyridine / 12 h / 20 °C2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C4: NaH / tetrahydrofuran / 12 h / -20 °C5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C6: 92 percent / NaOH; H2O / tetrahydrofuran / 48 h / 20 °C
参考文献
Robins, Morris J.; Miles, Robert W.; Samano, Mirna C.; Kaspar, Roger L. Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8204 - 8210
反应条件
Multi-step reaction with 5 steps 1: 100 percent / pyridine / 12 h / 20 °C2: 95 percent / Me2BBr; Et3N / CH2Cl2 / 1 h / -78 °C3: 89 percent / Et3N / tetrahydrofuran; acetonitrile / 48 h / 20 °C4: NaH / tetrahydrofuran / 12 h / -20 °C5: 112 mg / TBAF / tetrahydrofuran / 1 h / 20 °C
参考文献
Robins, Morris J.; Miles, Robert W.; Samano, Mirna C.; Kaspar, Roger L. Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8204 - 8210
