Hydrochloric Acid → (2R,3R,4S,5R)-2-[6-[(3-iodophenyl)methylamino]purin-9-yl]-5-(methoxymethyl)oxolane-3,4-diol

반응식

Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([O:18]C(=O)C)[C@H:12]1[O:13]C(=O)C.[I:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32].Cl>>[I:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH:32][C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[CH:9][N:10]=1)[C@@H:11]1[O:23][C@H:22]([CH2:24][O:25][CH3:26])[C@@H:17]([OH:18])[C@H:12]1[OH:13]

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 970123-Iodobenzylamine

HCID 109490246-chloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purine

생성물 1

HCID 10345757(2R,3R,4S,5R)-2-[6-[(3-iodophenyl)methylamino]purin-9-yl]-5-(methoxymethyl)oxolane-3,4-diol

실험 절차

Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 363 mg, 0.94 mmol) and 3-iodobenzylamine.HCl (1.41 mmol, 380 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 397 mg (0.80 mmol, 85%), mp 155–157° C.; Rf 0.54 (eluens 10% MeOH in CH2Cl2); 1H NMR (DMSO-d6) δ 8.40 (bs, 1H, NH), 8.33 (s, 1H, H-8), 8.21 (s, 1H, H-2), 7.70 (s, 1H, CCHCI), 7.57 (d, 1H, J=6.52 Hz, CCHCHCH), 7.34 (d, 1H, J=5.15 Hz, CCHCH), 7.08 (t, 1H, J=8.93 Hz, CCHCH), 5.89 (d, 1H, J=4.12 Hz, H-1′), 5.50–5.47 (m, 1H, OH-2′), 5.27–5.25 (m, 1H, OH-3′), 4.68–4.56 (m, 3H, H-2′, NHCH2), 4.14–4.13 (m, 1H, H-3′), 4.01–3.98 (m, 1H, H-4′), 3.57–3.53 (m, 2H, H-5′), 3.31 (s, 3H, OCH3); MS m/z 498 (M+H)+; Anal. (C18H20N5O4) C, H, N.