4.1.39  (2R,5R)-2-(6-amino-9H-purin-9-yl)-5-{[(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)[(4-chlorophenyl)methyl]amino]methyl}oxolane-3,4-diol (16)
Using method C with 36 (172 mg, 0.18 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 16 (45 mg, 37%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.36 (s, 1H), 8.25 (s, 1H), 8.13 (s, 1H), 8.11 (s, 1H), 7.34 (br. s, 2H), 7.25 (br. s, 2H), 7.23–7.17 (m, 2H), 7.17–7.11 (m, 2H), 6.00 (d, J = 6.2 Hz, 1H), 5.84 (d, J = 5.0 Hz, 1H), 5.45–5.39 (m, 2H), 5.27 (d, J = 4.8 Hz, 1H), 5.12 (d, J = 5.4 Hz, 1H), 4.58 (q, J = 5.5 Hz, 1H), 4.48 (dd, J = 6.2 Hz, J = 4.8 Hz, 1H), 4.30 (td, J = 4.6 Hz, J = 2.9 Hz, 1H), 4.04 (q, J = 5.1 Hz, 1H), 4.02–3.96 (m, 2H), 3.70–3.63 (m, 2H), 3.60–3.48 (m, 4H), 2.80 (dd, J = 14.0 Hz, J = 4.5 Hz, 1H), 2.67 (dd, J = 13.9 Hz, J = 7.0 Hz, 1H), 2.61 (q, J = 6.1 Hz, 2H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.2, 156.0, 152.6, 152.5, 149.3, 149.0, 139.8, 139.7, 138.2, 131.1, 130.4, 127.8, 119.3, 119.16, 87.67, 86.3, 86.1, 82.4, 81.2, 72.4, 71.8, 69.0, 67.5, 61.5, 57.5, 55.8, 52.9. HRMS (ESI+): m/z calcd for C29H35N11O7Cl [M+H]+: 684.2404, Found 684.2398.