Synthesis of a cytosine nucleoside of 2-amino-2-deoxy-beta-D-xylofuranose.
1-(2-Amino-2-deoxy-beta-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-(trifluoroacetamido)-beta-D-xylofuranosyl]uracil (6) by treatment with phosphorus pentasulfide in pyridine followed by amination of the resulting 4-thionucleoside 12 with metanolic ammonia. The best yield was obtained via route (a).
D002852:Chromatography, Ion Exchange; D003596:Cytosine / Q000032:analysis* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation; D013329:Structure-Activity Relationship; D013889:Thiouracil; D014994:Xylose
D013889:Thiouracil; D003596:Cytosine; D014994:Xylose