Hydrazine hydrate (1:1) → 5'-Deoxy-5'-[(2-hydrazinocarbonylethyl)methylamino]-adenosine sulfate

Participants

Reaction Steps

The procedure was the same as reported above for 13k using 13g (95 mg, 0.25 mmol) and hydrazine monohydrate (63 mg, 0.06 mL, 1.25 mmol): yield 39 mg (43%), MS: m/z 367 (M+H)+; 1HNMR (D2O) δ 8.47 (s, 1H, H-8), 8.45 (s, 1H, H-2), 6.17 (d, 1H, H-1′, J1′,2′=4.7 Hz), 4.90 (dd, 1H, H-2′, J2′,3′=5.2 Hz), 4.56-4.60 (bm, 1H, H-4′), 4.48 (dd, 1H, H-3′, J3′,4′=5.0 Hz), 3.82 (dd, 1H, 5′-CH2), 3.66 (dd, 1H, 5′-CH2), 3.59 (bt, 2H, N(CH3)—CH2), 2.97 (s, 3H, N—CH3), 2.86 (t, 2H, NHCO—CH2); UV λmax, nm, pH 1, 256.8 (∈ 16,600), pH 7, 258.5 (∈ 16,800), pH 13, 259.5 (∈ 17,600). Anal. (C14H22N8O4.2.0H2SO4.2.0H2O) C, H, N.

Provenance & Evidence