Chemical Name: 5-[1(R)-2,2-Dibromocyclopropyl]-2'-deoxyuridine; 1-(2-Deoxy-beta-D-ribofuranosyl)-5-[(1R)-2,2-dibromocyclopropyl]uracil; 1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-5-[1(R)-2,2-dibromocyclopropyl]-1H,3H-pyrimidine-2,4-dione
项目整合开发状态: Biological Testing
项目研究机构: University of Alberta (Originator)
合成路线:The reaction of 5-vinyl-2'-deoxyuridine (I) with benzoyl chloride in the presence of pyridine and diisopropylethylamine gives 3,3',5'-tribenzoyl-5-vinyl-2'-deoxyuridine (II).Subsequent reaction of (II) with phenyl(tribromomethyl)mercury in benzene at reflux yields a mixture of 5-[(1S)-2.2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (III,m.p.220 C) and 5-[(1R)-2,2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (IV,m.p.228 C) diastereomers which are separated by silica gel column chromatography (1:1 ratio) using a solvent gradient starting with toluene and ending with toluene: ethyl acetate (19:1 v/v).The absolute configuration of 5-[(1S)-2,2-dibromocyclopropyl]-2'-deoxyuridine (V),obtained by treatment of III with ammonia in methanol,was established by single crystal X-ray analysis.Treatment of IV with ammonia in methanol,to remove the benzoyl protecting groups,affords MW-60U.
📄 详细内容
合成路线:The reaction of 5-vinyl-2'-deoxyuridine (I) with benzoyl chloride in the presence of pyridine and diisopropylethylamine gives 3,3',5'-tribenzoyl-5-vinyl-2'-deoxyuridine (II).Subsequent reaction of (II) with phenyl(tribromomethyl)mercury in benzene at reflux yields a mixture of 5-[(1S)-2.2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (III,m.p.220 C) and 5-[(1R)-2,2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (IV,m.p.228 C) diastereomers which are separated by silica gel column chromatography (1:1 ratio) using a solvent gradient starting with toluene and ending with toluene: ethyl acetate (19:1 v/v).The absolute configuration of 5-[(1S)-2,2-dibromocyclopropyl]-2'-deoxyuridine (V),obtained by treatment of III with ammonia in methanol,was established by single crystal X-ray analysis.Treatment of IV with ammonia in methanol,to remove the benzoyl protecting groups,affords MW-60U.
参考文献标题:Structure of 1-(2-deoxy-beta-D-ribofuranosyl)-5-[(1S)-2,2-dibromocyclopropyl]uracil
文献作者:Tandon,M.; Moore,S.; Knaus,E.; Wiebe,L.; Santarsiero,B.; Lin,T.; James,M.
参考来源:Acta Cryst Sect C 1989,45647
合成路线:The reaction of 5-vinyl-2'-deoxyuridine (I) with benzoyl chloride in the presence of pyridine and diisopropylethylamine gives 3,3',5'-tribenzoyl-5-vinyl-2'-deoxyuridine (II).Subsequent reaction of (II) with phenyl(tribromomethyl)mercury in benzene at reflux yields a mixture of 5-[(1S)-2.2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (III,m.p.220 C) and 5-[(1R)-2,2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (IV,m.p.228 C) diastereomers which are separated by silica gel column chromatography (1:1 ratio) using a solvent gradient starting with toluene and ending with toluene: ethyl acetate (19:1 v/v).The absolute configuration of 5-[(1S)-2,2-dibromocyclopropyl]-2'-deoxyuridine (V),obtained by treatment of III with ammonia in methanol,was established by single crystal X-ray analysis.Treatment of IV with ammonia in methanol,to remove the benzoyl protecting groups,affords MW-60U.
参考文献标题:Synthesis,separation and absolute configuration of the two 5-(2,2-dibromocyclopropyl) and four 5-(2-bromocyclopropyl)diastereomers of 2'-deoxyuridine
文献作者:Tandon,M.; Knaus,E.; Wiebe,L.
参考来源:Can J Chem 1989,671484
合成路线:The reaction of 5-vinyl-2'-deoxyuridine (I) with benzoyl chloride in the presence of pyridine and diisopropylethylamine gives 3,3',5'-tribenzoyl-5-vinyl-2'-deoxyuridine (II).Subsequent reaction of (II) with phenyl(tribromomethyl)mercury in benzene at reflux yields a mixture of 5-[(1S)-2.2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (III,m.p.220 C) and 5-[(1R)-2,2-dibromocyclopropyl]-3,3',5'-tribenzoyl-2'-deoxyuridine (IV,m.p.228 C) diastereomers which are separated by silica gel column chromatography (1:1 ratio) using a solvent gradient starting with toluene and ending with toluene: ethyl acetate (19:1 v/v).The absolute configuration of 5-[(1S)-2,2-dibromocyclopropyl]-2'-deoxyuridine (V),obtained by treatment of III with ammonia in methanol,was established by single crystal X-ray analysis.Treatment of IV with ammonia in methanol,to remove the benzoyl protecting groups,affords MW-60U.
参考文献标题:MW-60U
文献作者:Knaus,E.E.; Wiebe,L.I.; Tandon,M.; Tyrrell,D.L.; Tovell,D.R.
参考来源:Drugs Fut 1989,14(12),1163