Abstract
1-(2-Amino-2-deoxy-β- D-xylofuranosyl)cytosine ( 13) was synthesized by three routes: ( a) coupling of 2-deoxy-3,5-di- O-p-nitrobenzoyl-2-(trifluoroacetamido)- D- xylofuranosyl chloride ( 5) with 2,4-dimethoxypyrimidine and subsequent treatment with methanolic ammonia ( b) coupling of 5 with 4- N-acetyl-2- O,4- N-bis(trimethylsilyl)cytosine followed by treatment with methanolic ammonia, and ( c) thiation of 1-[3,5-di- O-acetyl-2-deoxy-2-(triflouroacetamido)-β- D-xylofuranosyl]uracil ( 6) by treatment with phosphorus pentasulfide in pyridine followed by amination of the resulting 4-thionucleoside 12 with methanolic ammonia. The best yield was obtained via route ( a).
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