1-Hexene → HCID 69538227, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-propylaminoadenosine (9, 400 mg, 0.89 mmol) and (E)-1-borocatechol)-1-hexene (2.67 mmol). The mixture was purified by column chromatography (10% MeOH in CH2Cl2). Yield 43 mg (0.11 mmol, 12%), mp 170–172÷C; Rƒ 0.41 (10% MeOH in CH2Cl2); 1H NMR (MeOD-d4) δ 6.93–6.82 (m, 1H, ═CHCH2), 6.29 (d, 1H, J=15.48 Hz, ═CH), 6.04 (d, 1H, J=7.65 Hz, H-1′), 4.79–4.74 (m, 1H, H-2′), 4.29–4.26 (m, 1H, H-3′), 4.13–4.12 (m, 1H, H-4′), 3.81 (q, 2H, J=8.24 Hz, H-5′), 3.37–3.32 (m, 2H, NHCH2), 2.24 (q, 21H, J=7.16 Hz, ═CHCH2), 1.89–1.66 (m, 2H, NHCH2CH2), 1.51–1.35 (m, 4H, CH2CH2), 1.02–0.91 (m, 6H, 2×CH3); MS m/z 407 (M+H)+; HPLC, System A: 20–100% CH3CN in H2O in 35 min., retention time=8.10 min.; System B: 30–100% CH3OH in H2O in 40 min., retention time=20.25 min.

Provenance & Evidence