Syntheses of Potential Antimetabolites. XX. Syntheses of 5-Carbomethoxymethyl-and 5-Methylaminomethyl-2-thiouridine (The "First Letters"of Some Anticodons) and Closely Related Nucleosides from Uridine

Abstract

A procedure for the preparation of 5-substituted 2-thiouridines from uridine has been developed, whereby 5-carbomethoxymethyl-(8b) and 5-methylaminomethyl-2-thiouridine (10) (each may be the first letter of certain anticodons of some transfer ribonucleic acids) and the closely related nucleosides [e.g., 5-hydroxymethyl-2-thiouridine (11), 5-cyanomethyl-2-thiouridine (6b), and 5-carbomethoxymethyluridine (8b)] were prepared in satisfactory yields. Acylation of 5-methylaminomethyl-2-thiouridine (10) was also examined and 5-(N-methylbenzamido) methyl-2-thiouridines (12) was prepared and characterized.