Tecadenoson , CVT-510
Chemical Name: N6-[3(R)-Tetrahydrofuranyl]adenosine; (2R,3R,4S,5R)-2-(Hydroxymethyl)-5-[6-[tetrahydrofuran-3(R)-ylamino]-9H-purin-9-yl]tetrahydrofuran-3,4-diol
CAS No. 204512-90-3, 204512-92-5 ((S)-isomer), 343921-68-6 (deleted CAS), 204512-89-0 (undefined isomer)
项目整合开发状态: Phase III
项目研究机构: CV Therapeutics (Originator)
合成路线:The reaction of 3-tetrahydrofuroic acid (I) with diphenyl phosphoryl azide (DPPA) in refluxing dioxane gave the intermediate isocyanate (II),which was treated with benzyl alcohol (III) to yield carbamate (IV).Subsequent hydrogenolysis in the presence of Pd/C afforded racemic amine (V),which was resolved by treatment with S-(+)-10-camphorsulfonyl chloride (VI) in pyridine,followed by column chromatography and recrystallization from acetone of the resulting sulfonamide (VII).Then,hydrolysis in HCl-AcOH provided the S-amine (VIII).Condensation of amine (VIII) with 6-chloropurine riboside (IX) in the presence of triethylamine in refluxing MeOH furnished the title compound.
📌 参考资料/链接：
参考文献标题:N6 Heterocyclic substd.adenosine derivs.
文献作者:Lum,R.T.; Pfister,J.R.; Schow,S.R.; Wick,M.M.; Nelson,M.G.; Schreiner,G.F.(CV Therapeutics,Inc.)
参考来源:EP 0920438; EP 0992510; JP 2000501426; US 5789416; WO 9808855
📄 详细内容
合成路线:The reaction of 3-tetrahydrofuroic acid (I) with diphenyl phosphoryl azide (DPPA) in refluxing dioxane gave the intermediate isocyanate (II),which was treated with benzyl alcohol (III) to yield carbamate (IV).Subsequent hydrogenolysis in the presence of Pd/C afforded racemic amine (V),which was resolved by treatment with S-(+)-10-camphorsulfonyl chloride (VI) in pyridine,followed by column chromatography and recrystallization from acetone of the resulting sulfonamide (VII).Then,hydrolysis in HCl-AcOH provided the S-amine (VIII).Condensation of amine (VIII) with 6-chloropurine riboside (IX) in the presence of triethylamine in refluxing MeOH furnished the title compound.
参考文献标题:Tecadenoson
文献作者:Sorbera,L.A.; Bay閟,M.; Castar,J.; Mart韓,L.
参考来源:Drugs Fut 2002,27(9),846
产品链接: CAS No. 204512-90-3››