Compound 12

N 6-geranyladenosine

From: Mycobacterium tuberculosis releases an antacid that remodels phagosomes

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Synonyms:
  • (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.