Pyridine → 5'-Chloro-5'-deoxy-8-ethyladenosine

Participants

Reaction Steps

The procedure was the same as reported above for 3a using 2b40 (1.28 g, 4.33 mmol), pyridine (685 mg, 0.70 mL, 8.65 mmol), CH3CN (10 mL), and SOCl2 (2.57 g, 1.58 mL, 21.60 mmol): yield 498 mg (37%); MS m/z 314 (M+H)+; 1HNMR (DMSO-d6) δ 8.09 (bs, 1H, H-2), 7.14 (bs, 2H, 6-NH2), 5.80 (d, 1H, H-1′, J1′,2′=5.7 Hz), 5.48 (d, 1H, 2′-OH, J2′-2′OH=6.1 Hz), 5.45 (d, 1H, 3′-OH, J3′-3′OH=5.4 Hz), 5.20 (ddd, 1H, H-2′, J1′,2′=5.7 Hz, J2′,3′=4.6 Hz, J2′-2′OH=6.1 Hz), 4.30-4.37 (bm, 1H, H-3′), 4.03-4.10 (bm, 1H, H-4′), 3.94-4.0 (m, 1H, 5′-CH2), 3.83-3.89 (m, 1H, 5′-CH2), 2.89 (q, 2H, 8-CH2CH3), 1.31 (t, 3H, 8-CH2CH3).

Provenance & Evidence