Synthesis of 1-(3-deoxy-beta-D-psicofuranosyl)uracil and related compounds.
D-Fructose affords on treatment with cyanamide 2-amino-beta-D-fructofuro[2',3':3,4]-oxazoline which is not isolated but transformed directly by the reaction with ethyl propiolate into O(2,3)-anhydro-2-[beta-D-fructofuranosyl]uracil. This compound is benzoylated to the 1',4',6'-tri-O-benzoyl derivative by the action of benzoyl cyanide and triethylamine. On treatment with hydrogen chloride/dimethylformamide, the latter intermediate is converted to the 1-[1,4,6-tri-O-benzoyl-3-chloro-3-deoxy-beta-D-psicofuranosyl]uracil 1',4',5'-tribenzoate from which the title nucleoside derivative is obtained by methanolysis.
D002845:Chromatography; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D002942:Circular Dichroism; D003486:Cyanides; D003903:Deuterium; D004126:Dimethylformamide; D005069:Evaluation Studies as Topic; D006851:Hydrochloric Acid; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008968:Molecular Conformation; D009904:Optical Rotation; D010080:Oxazoles; D012822:Silicon Dioxide; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D003486:Cyanides; D010080:Oxazoles; D014498:Uracil; D012822:Silicon Dioxide; D004126:Dimethylformamide; D003903:Deuterium; D006851:Hydrochloric Acid