Reaction Steps
The reaction was performed with 2-iodo-8-benzylaminoadenosine (11, 410 mg, 0.82 mmol) and (E)-1-borocatechol)-1-hexene (2.47 mmol). The mixture was purified by column chromatography (10% MeOH in CH2Cl2). Yield 41 mg (0.10 mmol, 11%), mp 153–155÷C; 1H NMR (MeOD-d4) δ 7.64 (t, 1H, J=6.10 Hz, NH), 7.36–7.18 (m, 5H, phenyl), 6.59 (bs, 2H, NH2), 6.94–6.80 (m, 1H, ═CHCH2), 6.28 (d, 1H, J=15.42 Hz, ═CH), 5.92 (d, 1H, J=7.71 Hz, H-1′), 5.77 (t, 1H, J=4.85 Hz, OH-2′), 5.32 (d, 1H, J=6.74 Hz, OH-5′), 5.18 (d, 1H, J=4.18 Hz, OH-3′), 4.64 (q, 1H, J=4.64 Hz, H-2′), 4.58 (t, 2H, J=4.65 Hz, NHCH2), 4.09 (t, 1H, J=4.09 Hz, H-3′), 3.98 (d, 1H, J=1.60 Hz, H-4′), 3.62 (q, 2H, J=2.58 Hz, H-5′), 2.29–2.05 (m, 2H, ═CHCH2), 1.72–1.20 (m, 4H, CH2CH2), 1.00–0.83 (m, 3H, CH3) ppm; MS m/z 456 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=9.61 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=26.10 min.
