Further Confirmation of the Structure of 3′-(2-Pyridyldithio)-3′-deoxyadenosine and 3′-Thio-3′-deoxyadenosine: Synthetic Convergence with Cordycepin

3′-Deoxynucleosides have demonstrated
profound
biochemical
utility, including in our recent work on the use of aminoacyl thio-tRNAs
for in vitro translation. Though our preparation of 3′-(2-pyridyldithio)-3′-deoxyadenosinea
key synthetic precursor en route to aminoacyl thio-tRNAsfollowed
robust prior precedents, an unrelated recent structural revision prompted
us to validate the regioselectivity of our route further. Here we
provide confirmatory evidence for the structure of 3′-(2-pyridyldithio)-3′-deoxyadenosine
and downstream analogues via synthetic convergence with a 3′-deoxynucleoside
antibiotic, cordycepin, and concomitant MicroED analysis.