Synthesis of some purine and pyrimidine nucleosides of 3-Amino-2,3,6-trideoxy- l- lyxo-hexopyranose (daunosamine)

• Published in: Carbohydrate research 1977-06, Vol.56 (1), p.35-42
• Main Authors: Lazzari, Ettore, Vigevani, Aristide, Arcamone, Federico
• Format: Article
• Language: English
• Subjects: Adenosine - analogs & derivatives; Cytidine - analogs & derivatives; Deoxy Sugars; Hexosamines; Magnetic Resonance Spectroscopy; Methods; Molecular Conformation; Optical Rotation; Purine Nucleosides - chemical synthesis; Puromycin - analogs & derivatives; Pyrimidine Nucleosides - chemical synthesis; Thymidine - analogs & derivatives
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(00)84234-2

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-trifluoro-acetyl-α-daunosaminyl chloride either with N 6-benzoyl-9-chloromercuryadenine in boiling xylene or with N 5-benzoyladenine in dichloromethane at room temperature in the presence of a molecular sieve. In each reaction, the β-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-β-Daunosaminyl-6-dimethylaminopurine was coupled to N-benzyloxycarbonyl- O-methyltyrosine, giving, after hydrogenolysis, the daunosaminyl analogue of puromycin.