Ethanol → (2s,3r,5s)-5-(6-Amino-9h-Purin-9-Yl)-Tetrahydro-2-(Hydroxymethyl)furan-3-Ol

Participants

Reaction Steps

mp 189-190° C. (EtOH 95) (identical to commercial 2′-deoxy-D-adenosine) 1H NMR (200 MHz, DMSO-D6): δ8.35 and 8.14 (2s, 2H, H2 and H8), 7.34 (s1, 2H, NH2), 6.35 (dd, 1H, H1′, J 6.1 Hz, J 7.85 Hz), 5.33 (d, 1H, OH2′, J 4.0 Hz), 5.28 (dd, 1H, H3′, J 4.9 Hz; J 6.6 Hz), 4.42 (m, 1H, OH5′), 3.88 (m, 1H, H4′), 3.63−3.52 (m, 2H, H5′a and H5′b), 2.71 (m, 1H, H2′a), 2.28 (m, 1H, H2′b). (identical to commercial 2′-deoxy-D-adenosine) αD+26° (c 0.5 water) (commercial 2′-deoxy-D-adenosine −25° (c 0.5 water)). UV λmax 260 nm (ε 14100) (H2O). Mass analysis (FAB+, GT) m/z 252 (M+H)+, 136 (BH2)+

Provenance & Evidence