Hydrochloric Acid → HCID 66906212, compound

Participants

Reaction Steps

1 M HCl (10 ml) was added to a solution of 8-ethoxyvinyladenosine (17k) (1.48 g, 4.37 mmol) in THF (40 ml) and the solution stirred at room temperature for 20 h. Aqueous K2CO3 was added to neutral pH and the mixture applied directly onto a flash chromatography silica gel column which was developed with 15% MeOH in CH2Cl2; yield 1.17 g (87%). 1H NMR: (300 MHz, DMSO-d6); δ 2.72 (3H, s, COCH3), 3.52-3.71 (2H, m, H-5′), 3.94-3.96 (1H, m, H-4′ el. H-3′), 4.10-4.23 (1H, m, H-3′ or H-4′), 4.94 (1H, m, H-2′), 5.11 (1H, d, J 4.4 Hz, 3′-OH), 5.24 (1H, d, J 6.1 Hz, 2′-OH), 5.56-5.59 (1H, m, 5′-OH), 6.76 (1H, d, J 6.5 Hz, H-1′), 7.87 (2H, s, NH2), 8.21 (1H, s, H-2). 13C NMR: (75 MHz, DMSO-d6); δ 27.9 (CH3), 62.3 (C-5′), 70.9/72.0 (C-2′, C-3′), 86.3/89.3 (C-4′, C-1′), 118.7 (C-5), 143.7/150.5/154.7/157.7 (C-6, C-8, C-2, C-4), 191.7 (CO).

Provenance & Evidence