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Yield: 90%. Solid. Mp 103–106°C. Rf = 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 63.3 (c 1, CH2Cl2); IR (KBr, cm−1): 3400, 3100, 2950, 1716, 1428, 1395, 1237, 1042, 718. 1H NMR (300 MHz, DMSO-d6): δ 2.02 (s, 3H, CH3CO), 2.06 (s, 3H, CH3CO), 3.94–4.03 (m, 3H, NCH2 and H-5), 4.11–4.16 (m, 2H, H-6 and H-6′), 4.56–4.70 (m, 4H, OCH2 and NCH2Phth), 5.09 (bs, 1H, H-1), 5.20 (dd, 1H, J = 9.6 and 1.5 Hz, H-4), 5.83–5.85 (m, 2H, H-2 and H-3), 7.84 (m, 4H, phthalimide), 8.18 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 37.6, 47.9, 61.2, 62.0, 65.2, 66.9, 93.4, 123.6, 127.5, 129.4, 131.6, 134.3, 167.6, 170.3, 170.8. Anal. Calc. for C23H24N4O8: C, 57.02; H, 4.99; N, 11.56. Found: C, 57.29; H, 5.36; N, 11.42.
Yield: 81%. Solid. Mp 125–127°C. Rf 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 49.6 (c 1, CH2Cl2); IR (KBr, cm−1): 3468, 2925, 2854, 1770, 1710, 1491, 1399, 1231, 1037, 722. 1H NMR (300 MHz, DMSO-d6): δ 2.03 (s, 3H, CH3CO), 2.05 (s, 3H, CH3CO), 2.18 (q, 2H, NCH2), 3.61 (t, 2H, J = 6.9 Hz, NCH2), 3.98 (ddd, 1H, J = 9.3, 5.1 and 3.0 Hz, H-5), 4.12–4.15 (m, 2H, H-6 and H-6′), 4.42 (t, 2H, J = 6.9 Hz), 4.59 (d, 1H, J = 12 Hz, OCHa), 4.72 (d, 1H, J = 12.3 Hz, OCHb), 5.17 (s, 1H, H-1), 5.20 (d, 1H, J = 9.6 Hz, H-4), 5.86 (bs, 2H, H-2 and H-3), 7.82–7.87 (m, 4H, phthalimides), 8.12 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 29.4, 34.9, 47.2, 60.5, 62.8, 65.2, 67.0, 93.8, 122.0, 123.4, 127.5, 128.8, 129.5, 131.7, 134.3, 143.3, 168.3, 170.3, 170.9. Anal. Calc. for C24H26N4O8: C, 57.83; H, 5.26; N, 11.24. Found: C, 57.88; H, 5.46; N, 11.14.
Yield: 68%. Solid. Mp 103–106°C. Rf 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 37.9 (c 1, CH2Cl2); IR (KBr, cm−1): 3464, 3141, 2935, 1769, 1711, 1437, 1398, 1370, 1230, 1038, 721. 1H NMR (400 MHz, DMSO-d6): δ 1.54–1.60 (q, 2H, CH2), 1.82–1.85 (q, 2H, CH2), 2.03 (s, 3H, CH3CO), 2.05 (s, 3H, CH3CO), 3.60 (t, 2H, J = 6.8 Hz, NCH2), 3.98 (ddd, 1H, J = 8.8, 5.2 and 3.2 Hz, H-5), 4.09–4.17 (m, 2H, H-6 and H-6′), 4.37 (t, 2H, J = 6.8 Hz), 4.60 (d, 1H, J = 12.4 Hz, OCHa), 4.72 (d, 1H, J = 12.4 Hz, OCHb), 5.17 (s, 1H, H-1), 5.20 (d, 1H, J = 9.6 Hz, H-4), 5.86 (bs, 2H, H-2 and H-3), 7.82–7.87 (m, 4H, phthalimides), 8.10 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 25.5, 27.4, 29.6, 36.7, 49.4, 61.4, 62.7, 65.1, 66.9, 93.7, 122.7, 123.2, 127.4, 129.4, 131.8, 134.0, 144.0, 168.3, 170.2, 170.8. Anal. Calc. for C25H28N4O8: C, 58.59; H, 5.51; N, 10.93. Found: C, 58.47; H, 5.30; N, 10.56.
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