Acetic Acid → Thymidine

Participants

Reaction Steps

To a stirred solution of 3′-deoxy-3′-C-formyl-5′-O-tritylthymidine (0.59, 1 mmol, prepared as per Example 4 in CH2Cl2:MeOH (2:1, 30 vol.) was added AcOH (0.5 ml) and methoxyamine hydrochloride (0.189, 2.2 mml) at room temperature. The mixture was stirred for 30 min., concentrated under vacuum and the residue dissolved in MeOH (20 ml). To this solution, concentrated HCl (0.1 ml) was added and stirred for 1 h. The solution was neutralized with NH4OH (≈2 ml) and concentrated under a vacuum to furnish the 3′-C-[(methoxyimido)methyl] derivative of thymidine. 1H NMR (CDCl3) δ 9.67 (s, 1, NH); 7.67 (s, 1, H-6); 7.33 (d, 0.70, H-3″ E isomer), 6.65 (d, 0.30, H-3′ Z isomer); 6.15 (m, 1, H-1′); 3.60-4.12 (m, 3.3, H-4′, H-5′5″, H-3′ Z isomer); 3.91 (s, 0.9, OCH3 Z isomer); 3.82 (s, 2.1, OCH3 oxime E isomer); 3.26 (m, 0.7, H-3′ E isomer); 2.27-2.60 (m, 2, H-2′,2″); 1.91 (2s, 3, C6CH3).

Provenance & Evidence