SYNTHESIS OF URACIL AND THYMINE NUCLEOSIDES OF UNSATURATED 5-(AMINOACYL)AMINOPENTOFURANOSES

Improved syntheses of 1-(2,3-dideoxy-β-d-glycero-pent-2-enofuranosyl)-uracil (5a) and -thymine (5b) have been achieved via treatment of the corresponding 3′,5′-oxetane with sodium hydroxide in hexamethylphosphoric triamide. The 2′,3′-unsaturated nucleosides (5a and 5b) were converted into 1-(5-amino-2,3,5-trideoxy-β-d-glycero-pent-2-enofuranosyl)-uracil (8a) and -thymine (8b), respectively. A new type of aminoacyl nucleoside, the 1-[5-(aminoacyl)amino-2,3,5-trideoxy-β-d-glycero-pent-2-enofuranosyl)-uracils and -thymines, has been obtained by condensation of 8a and 8b with the active esters of several amino acid derivatives followed by deprotection. These nucleosides were examined for in vivo antitumor activity against Sarcoma 180 (solid tumor). However, none of the compounds exhibited significant antitumor activity. © 1979.