Synthesis in Nucleoside Antibiotics

Part III. Synthesis of 4-Amino-5-cyano-6-methylmercaptopyrrolo-[2, 3-d] pyrimidine-7-β-D-ribosides (Toyocamycin Analogs)

Abstract

Both ribofuranoside (3) and ribopyranoside (5) of 4-amino-5-cyano-6-methylmercaptopyr-rolo[2, 3-d]pyrimidine (analogs of toyocamycin) have been synthesized for the first time by the fusion procedure using bis-(p-nitrophenyl) hydrogen phosphate as catalyst. Evidence for the β-configuration has been provided by analyzing the NMR spectra and ORD curves. The tumor-inhibitory activity of 3 against Ehrlich ascites carcinoma in mice has also been examined.