1-Hexyne → HCID 69538203, compound

Participants

Reaction Steps

The reaction was performed with 2-iodo-8-butylaminoadenosine (10, 200 mg, 0.43 mmol) and 1-hexyn (2.08 mmol). The mixture was purified by column chromatography (5% MeOH in CH2Cl2). Yield 111 mg (0.26 mmol, 62%), mp 182–184÷C; 1H NMR (DMSO-d6) δ 6.95 (t, 1H, J=5.49 Hz, NH), 6.55 (bs, 2H, NH2), 5.87 (d, 1H, J=7.90 Hz, H-1′), 5.77–5.72 (m, 1H, OH-2′), 5.26 (d, 1H, J=6.52 Hz, OH-5′), 5.15 (d, 1H, J=4.12 Hz, OH-3′), 4.54 (q, 1H, J=5.84 Hz, H-2′), 4.09–4.04 (m, 1H, H-3′), 3.95–3.93 (m, 1H, H-4′), 3.64–3.59 (m, 2H, H-5′), 3.09 (m, 2H, NHCH2), 2.36 (m, 2H, ≡CCH2), 1.51–1.30 (m, 8H, 2×CH2CH2), 0.89 (t, 6H, J=,7.55 Hz, 2×CH3); MS m/z 419 (M+H)+; Anal. (C20H30N6O4) C, H, N.

Provenance & Evidence