Synthesis of some purine and pyrimidine nucleosides of 3-amino-2,3,6-trideoxy-L-lyxo-hexopyranose (daunosamine).
The daunosaminyl analogue of the antibiotic puromycin and the nucleoside derivatives of daunosamine with adenine, thymine, and cytosine have been synthesised. The nucleoside derivatives of 6-dimethylaminopurine, thymine, and cytosine were prepared by melting the protected daunosamine with the protected base in vacuo. Daunosaminyladenine was obtained by condensing N-trifluoroacetyl-O-trifluoroacetyl-alpha-daunosaminyl chloride either with N6-benzoyl-9-chloromercuryadenine in boiling xylene or with N6-benzoyladenine in dichloromethane at room temperature in the presence of a molecular sieve. In each reaction, the beta-anomeric nucleoside was obtained, as shown by p.m.r. data. The protecting groups were removed with barium hydroxide or methanolic ammonia to give the free aminonucleosides in good yield. 9-beta-Daunosaminyl-6-dimethylaminopurine was coupled to N-benzylocyxcarbonyl-O-methyltyrosine, giving, after hydrogenolysis, the daunosaminyl analogue of puromycin.
D000241:Adenosine / Q000031:analogs & derivatives; D003562:Cytidine / Q000031:analogs & derivatives; D003837:Deoxy Sugars; D006595:Hexosamines; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D008968:Molecular Conformation; D009904:Optical Rotation; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011691:Puromycin / Q000031:analogs & derivatives; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013936:Thymidine / Q000031:analogs & derivatives
D003837:Deoxy Sugars; D006595:Hexosamines; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; C007217:daunosamine; D011691:Puromycin; D003562:Cytidine; D000241:Adenosine; D013936:Thymidine