title: Syntheses of 1-beta-D-arabinofuranosyl-5-hydroxymethyl-N4-alkylcytosine.
abstract: Starting from uridine, 1-beta-D-arabinofluranosyl-5-hydroxymethyl-N4-alkylcytosines were prepared via 1-beta-D-arabinofuranosyluracil. During the course of this synthetic work, an interesting observation has been made that 5-acetoxy group of 1-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)-5-acetoxymethyluracil and its derivatives was easily displaced at room temperature with alkylamine in methanol, but not in chloroform, to give the corresponding 5-alkylaminomethyl derivatives.
mesh_terms: D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008722:Methods; D014529:Uridine
chemical_list: D007202:Indicators and Reagents; D003561:Cytarabine; D014529:Uridine