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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.
E Lazzari, and
A Vigevani, and
F Arcamone
November 1975,
Carbohydrate research,
E Lazzari, and
A Vigevani, and
F Arcamone
April 1989,
Carbohydrate research,
E Lazzari, and
A Vigevani, and
F Arcamone
January 1990,
Carbohydrate research,
E Lazzari, and
A Vigevani, and
F Arcamone
July 1975,
Journal of medicinal chemistry,
E Lazzari, and
A Vigevani, and
F Arcamone
February 1976,
Carbohydrate research,
E Lazzari, and
A Vigevani, and
F Arcamone
January 2000,
Chemical & pharmaceutical bulletin,
E Lazzari, and
A Vigevani, and
F Arcamone
August 2003,
Organic letters,
E Lazzari, and
A Vigevani, and
F Arcamone
November 1974,
Carbohydrate research,
E Lazzari, and
A Vigevani, and
F Arcamone
July 2008,
The journal of physical chemistry. A,
E Lazzari, and
A Vigevani, and
F Arcamone
May 1977,
Carbohydrate research,
