Thioglycolic Acid → 8-Carboxymethylthio-5'-azido-5'-deoxyadenosine

Participants

Reaction Steps

A solution of thioglycolic acid (0.2 mmol) and NaH (0.4 mmol, 60% in oil) in anhydrous DMF (2 mL) was stirred for 10 min, then 8-bromo-5′-azido-5′-deoxyadenosine (8) (50 mg, 0.13 mmol) in DMF (1 mL) was added at 0° C. After 8 h at room temperature, more thioglycolate (0.2 mmol) in DMF was added. After stirring overnight, the reaction mixture was concentrated to dryness and the residue purified by reverse phase HPLC (10-30% ACN in TEAA over 20 min) to give 10 (28 mg, 56%); UV λmax 279 nm; HRMS (ESI-TOF) m/z calcd for C12H14N8O5S (M+H) 383.0886; found 383.0890.

Provenance & Evidence