BRANCHED-CHAIN SUGAR NUCLEOSIDES .V. SYNTHESIS AND ANTIVIRAL PROPERTIES OF SEVERAL BRANCHED-CHAIN SUGAR NUCLEOSIDES

The synthesis of 3′-C-methylcytidine and its α-D anomer as well as 2′-C-methylcytidine, 2′-C-methyl-5-fluorocytidine, and 2′-C-methyl-5-fluorouridine via the Hilbert-Johnson reaction is described. In the synthesis of 2′-C-methylcytidine from N-acetylcytosinemercury a preponderance of the “O-glycoside” was formed. Biological testing indicates that 3′-C-methylcytidine as well as the previously synthesized 2′-and 3′-C-methyladenosines are effective antivaccinia agents in mice. © 1969, American Chemical Society. All rights reserved.