Nucleosides LXXXIX. Synthesis of 1-(2-chloro-2-deoxy-alpha- and -beta-D-arabinofuranosyl)cytosines.
1-(2-Chloro-2-deoxy-beta-D-arabinofuranosyl)cytosine (16) and its alpha anomer (18) were synthesized by direct condensation of 3,5-di-O-acetyl-2-chloro-2-deoxy-alpha-D-arabinofuranosyl bromide with trimethylsilylated N-4-acetylcytosine in the absence of catalyst. A new and convenient method for the synthesis of 1,3,5-tri-O-acetyl-2-chloro-2-deoxy-alpha-D-arabinofuranose from methyl 3,5-di-O-benzyl-alpha,beta-D-ribofuranoside is described.
D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D013237:Stereoisomerism
D003561:Cytarabine