1-Hexene → HCID 69538207, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-butylaminoadenosine (10, 380 mg, 0.82 mmol) and (E)-1-borocatechol)-1-hexene (2.46 mmol). The mixture was purified by column chromatography (10% MeOH in CH2Cl2). Yield 42 mg (0.10 mmol, 12%); Rƒ 0.44 (10% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.94–6.80 (m, 1H, ═CHCH2), 6.28 (d, 1H, J=15.42 Hz, ═CH), 6.02 (d, 1H, J=7.62 Hz, H-1′), 4.81–4.69 (m, 1H, H-2′), 4.31–4.20 (m, 1H, H-3′), 4.20–4.05 (m, 1H, H-4′), 3.87–3.70 (m, 2H, H-5′), 3.35–3.23 (m, 2H, NHCH2), 2.29–2.05 (m, 2H, ═CHCH2), 1.72–1.20 (m, 8H, 2×CH2CH2), 1.00–0.83 (m, 6H, 2×CH3); MS m/z 422 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=8.53 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=20.47 min.

Provenance & Evidence