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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Abstract
A procedure for the preparation of 5-substituted 2-thiouridines from uridine was developed, whereby 5-carbomethoxymethyl- and 5-methylaminomethyl-2-thiouridine (each may be the 1st letter of certain anticodons of some transfer RNA) and the closely related nucleosides [e.g., 5-hydroxymethyl-2-thiouridine, 5-cyanomethyl-2-thiouridine, and 5-carbomethoxymethyluridine were prepared in satisfactory yields. Acylation of 5-methylaminomethyl-2-thiouridine was also examined and 5-(N-methylbenzamido)methyl-2-thiouridines was prepared and characterized.