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结构式
乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
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乙二醇
甲醛
63148-62-9
MDI
丁酮
二甲基亚砜
碳酸氢钠
471-34-1
5-甲基尿甙
合成路线
（共 89 条）
102-09-0
碳酸二苯酯
+
1463-10-1
5-甲基尿甙
→
反应条件
22423-26-3
2,2'-O-脱水-5-甲基尿嘧啶核苷
反应条件
sodium hydrogencarbonate in N,N-dimethyl-formamide 1 h; Heating / reflux;
参考文献
Isis Pharmaceuticals Inc.
Patent: US2004/77085 A1, 2004 ;
Location in patent: Page/Page column 16 ;
102-09-0
碳酸二苯酯
+
1463-10-1
5-甲基尿甙
→
反应条件
22423-26-3
2,2'-O-脱水-5-甲基尿嘧啶核苷
+
139-02-6
苯酚钠
反应条件
sodium hydrogencarbonate in DMF (N,N-dimethyl-formamide) 1 h;
参考文献
ISIS PHARMACEUTICALS INC.
Patent: WO2005/14607 A2, 2005 ;
Location in patent: Page/Page column 90-91 ;
1463-10-1
5-甲基尿甙
→
反应条件
114672-74-1
反应条件
1: pyridine / 1.5 h 2: pyridine / CH2Cl2 / 1) ice-bath, 15 min; 2) 20 deg C, 3 h 3: aq. NaOH / ethanol / 1 h / 60 °C 4: 75 percent / LiEt3BH / tetrahydrofuran / 1) dry ice/acetone cooling, 1 h; 2) 20 deg C, 1 h 5: 74 percent / aq. AcOH / 0.5 h / 22 °C View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 31, # 7 p. 1475 - 1479
1463-10-1
5-甲基尿甙
→
反应条件
117174-39-7
反应条件
1: 68 percent / pyridine / 48 h / Ambient temperature 2: 73 percent / CrO3, pyridine, Ac2O / CH2Cl2 / 0.75 h / Ambient temperature 3: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 4: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 5: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 6: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 7: 93 percent / pyridine / 24 h / 18 °C 8: pyridine / CH2Cl2 / 2 h / Ambient temperature 9: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 10: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme
参考文献
Calvo-Mateo; Camarasa; Diaz-Ortiz; De Las Heras
Tetrahedron Letters, 1988 , vol. 29, # 8 p. 941 - 944
1463-10-1
5-甲基尿甙
→
反应条件
117174-38-6
反应条件
1: 68 percent / pyridine / 48 h / Ambient temperature 2: 73 percent / CrO3, pyridine, Ac2O / CH2Cl2 / 0.75 h / Ambient temperature 3: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 4: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 5: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 6: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 7: 93 percent / pyridine / 24 h / 18 °C 8: pyridine / CH2Cl2 / 2 h / Ambient temperature 9: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 10: 94 percent / 1N HCl / methanol / 0.5 h / Ambient temperature View Scheme
参考文献
Calvo-Mateo; Camarasa; Diaz-Ortiz; De Las Heras
Tetrahedron Letters, 1988 , vol. 29, # 8 p. 941 - 944
76-83-5
三苯基氯甲烷
+
124-63-0
甲烷磺酰氯
+
1463-10-1
5-甲基尿甙
→
反应条件
124493-84-1
反应条件
pyridine 1.) a) 0 deg C, overnight, b) 70 deg C, 3 h, 2.) a) 0 deg C, 1 h, b) RT, overnight; Yield given. Multistep reaction;
参考文献
Huang; Chen; Wang; Kim; Warshaw; Armstrong; Zhu; Chou; Watanabe; Matulic-Adamic; Su; Fox; Polsky; Baron; Gold; Hardy; Zuckerman
Journal of Medicinal Chemistry, 1991 , vol. 34, # 5 p. 1640 - 1646
1463-10-1
5-甲基尿甙
→
反应条件
124493-84-1
反应条件
1: pyridine / 20 °C 2: 5 h / 0 °C View Scheme
参考文献
Haraguchi, Kazuhiro; Itoh, Yoshiharu; Takeda, Shingo; Honma, Yosuke; Tanaka, Hiromichi; Nitanda, Takao; Baba, Masanori; Dutschman, Ginger E.; Cheng, Yung-Chi
Nucleosides, Nucleotides and Nucleic Acids, 2004 , vol. 23, # 4 p. 647 - 654
→
反应条件
110483-43-7
(2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷
反应条件
sodium hydroxide; hydrogen bromide in water; acetic acid; acetonitrile
参考文献
Ajinomoto Co., Inc.
Patent: US5625057 A1, 1997 ;
506-96-7
乙酰溴
+
1463-10-1
5-甲基尿甙
→
反应条件
110483-43-7
(2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷
反应条件
in acetonitrile Heating;
参考文献
Mansuri; Starrett Jr.; Wos; Tortolani; Brodfuehrer; Howell; Martin
Journal of Organic Chemistry, 1989 , vol. 54, # 20 p. 4780 - 4785
Title/Abstract Full Text View citing articles Show Details
Wilson; Hager; El-Kattan; Liotta
Synthesis, 1995 , # 12 p. 1465 - 1479
40635-67-4
2-乙酰氧基异丁酰溴
+
1463-10-1
5-甲基尿甙
→
反应条件
110483-43-7
(2Xi)-3',5'-二-O-乙酰基-2'-溴-2'-脱氧-3,4-二氢胸苷
反应条件
in acetonitrile 2 h; Heating; Title compound not separated from byproducts;
参考文献
Mansuri; Starrett Jr.; Wos; Tortolani; Brodfuehrer; Howell; Martin
Journal of Organic Chemistry, 1989 , vol. 54, # 20 p. 4780 - 4785
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