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.

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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.

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