Compound 12
N 6-geranyladenosine
From: Mycobacterium tuberculosis releases an antacid that remodels phagosomes
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- (2R,3R,4S,5R)-2-(6-(((E)-3,7-dimethylocta-2,6-dien-1-yl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Compound data: 1H NMR
Compound data: 13C NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
The title compound was synthesised following the general procedure outlined for compound 11. The product was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 8.21 (s, 1H), 7.90 (s, 1H), 5.88 (d, J = 6.1 Hz, 1H), 5.47 – 5.38 (m, 2H), 5.31 (t, J = 6.7 Hz, 1H), 5.19 (d, J = 4.5 Hz, 1H), 5.05 (t, J = 6.8 Hz, 1H), 4.61 (q, J = 5.8 Hz, 1H), 4.15 (q, J = 4.3 Hz, 1H), 4.08 (s, 2H), 3.97 (q, J = 3.4 Hz, 1H), 3.68 (dt, J = 12.1, 4.1 Hz, 1H), 3.55 (ddd, J = 11.7, 7.3, 3.6 Hz, 1H), 2.14 – 1.86 (m, 4H), 1.70 (s, 3H), 1.59 (s, 3H), 1.53 (s, 3H). 13C NMR (101 MHz, DMSO-d6) δ 154.35, 152.32, 148.25, 139.66, 136.65, 130.80, 123.95, 121.75, 119.80, 87.96, 85.89, 73.51, 70.65, 61.67, 39.04, 37.70, 25.97, 25.45, 17.54, 16.17. HRMS (ESI+, m/z): calculated for C20H30N5O4 [M+H]+: 404.2292; found: 404.2286.