1-Hexene → HCID 69538204, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-methylaminoadenosine (7, 520 mg, 1.23 mmol) and (E)-1-borocatechol)-1-hexene (3.70 mmol). The mixture was purified by column chromatography (20% MeOH in CH2Cl2). Yield 42 mg (1.11 mmol, 9%), mp 161–166÷C; Rƒ 0.60 (20% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.91–6.83 (m, 1H, ═CHCH2), 6.29 (d, 1H, J=15.44 Hz, ═CH), 5.98 (d, 1H, J=7.55 Hz, H-1′), 4.81–4.74 (m, 1H, H-2′), 4.29 (t, 1H, J=5.49 Hz, H-3′), 4.13 (m, 1H, H-4′), 3.82–3.79 (m, 2H, H-5′), 2.97 (m, 3H, NHCH3), 2.29–2.22 (m, 2H, ═CHCH2), 1.52–1.36 (m, 4H, CH2CH2), 0.94 (t, 3H, J=6.52 Hz, CH3); MS m/z 379 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=6.15 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=18.67 min.

Provenance & Evidence