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E. D. Chrysina et al. / Tetrahedron: Asymmetry 20 (2009) 733–740
17. Compound 3a. 1-(b-
D
-Glucopyranosyl)-4-phenyl-1,2,3-triazole: white solid.
22. Compound 5d. N-Hydroxyacetyl-b-D-glucopyranosylamine: white crystals. Mp:
Mp: 228–231 °C (lit.25 mp: 228–230 °C); [
a
]D = ꢁ69 (c 0.24, DMSO).
150–152 °C; [
a
]
D = ꢁ2 (c 0.22, MeOH); 1H NMR (CD3OD) d (ppm) 4.95 (1H, d,
18. Compound 3b. 1-(b-
D
-Glucopyranosyl)-4-(1-naphthyl)-1,2,3-triazole: colour-
J1,2 9.2 Hz, H-1), 4.05 (2H, s, CH2), 3.83 (1H, dd, J5,6a <1 Hz, J6a,6b 11.9 Hz, H-6a),
3.67 (1H, dd, J5,6b 5.3 Hz, H-6b), 3.46–3.31 (4H, m, H-2, H-3, H-4, H-5); 13C NMR
(CD3OD) d (ppm) 176.3 (CO), 80.7 (C-1), 79.7, 78.8, 73.8, 71.3 (C-2–C-5), 62.7,
62.6 (C-6, CH2). Anal. Calcd for C8H15NO7 (237.21): C, 40.51; H, 6.37; N, 5.90.
Found: C, 40.03; H, 6.30; N, 5.99.
less syrup. Rf: 0.35 (8:2 CHCl3–MeOH); [
a
]
D = ꢁ22 (c 0.21, MeOH); 1H NMR
(CD3OD) d (ppm) 8.48 (1H, s, triazole H), 8.20–7.44 (7H, m, aromatics), 5.75
(1H, d, J1 ,2 9.2 Hz, H-10), 4.05 (1H, pseudo t, J2 ,3 9.2, H-20), 3.91 (1H, dd, J5 ,6 a
0
0
0
0
0
0
<1 Hz, J6 a,6b 11.9 Hz, H-60a), 3.73 (1H, dd, J5 ,6 b 5.3 Hz, H-60b), 3.68–3.55 (3H,
m, H-30, H-40, H-50); 13C NMR (CD3OD) d (ppm) 147.5 (triazole C-4), 135.3,
132.3, 130.3, 129.5, 128.5, 127.2, 127.8, 126.4, 126.2, (aromatics), 124.5
(triazole C-5), 89.8 (C-10), 81.1, 78.4, 74.0, 70.8 (C-20–C-50), 62.3 (C-60). Anal.
Calcd for C18H19N3O5 (357.37): C, 60.50; H, 5.36; N, 11.76. Found: C, 60.42; H,
5.25; N, 11.69.
0
0
0
23. Akula, R.A.;Temelkoff, D.P.;Artis, N. D.;Norris,P.Heterocycles 2004,63, 2719–2725.
24. Chittaboina, S.; Xie, F.; Wang, Q. Tetrahedron Lett. 2005, 46, 2331–2336.
25. Rossi, L. L.; Basu, A. Bioorg. Med. Chem. Lett. 2005, 15, 3596–3599.
26. Wilkinson, B. L.; Bornaghi, L. F.; Poulsen, S.-A.; Houston, T. A. Tetrahedron 2006,
62, 8115–8125.
19. Compound 3c. 1-(b-
D
-Glucopyranosyl)-4-(2-naphthyl)-1,2,3-triazole: white
27. Oikonomakos, N. G.; Kontou, M.; Zographos, S. E.; Watson, K. A.; Johnson, L. N.;
Bichard, C. J. F.; Fleet, G. W. J.; Acharya, K. R. Protein Sci. 1995, 4, 2469–2477.
28. Saheki, S.; Takeda, A.; Shimazu, T. Anal. Biochem. 1985, 148, 277–281.
29. Oikonomakos, N. G.; Melpidou, A. E.; Johnson, L. N. Biochim. Biophys. Acta 1985,
832, 248–256.
30. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307–326.
31. CCP4. Acta Crystallogr. Sect. D 1994, 50, 760–763.
32. Watson, K. A.; Chrysina, E. D.; Tsitsanou, K. E.; Zographos, S. E.; Archontis, G.;
Fleet, G. W. J.; Oikonomakos, N. G. Proteins: Struct. Funct. Bioinform. 2005, 61,
966–983.
solid. Mp: 212–214 °C;
(ppm) 8.98 (1H, s, triazole H), 8.47 (1H, s, aromatic), 8.01–7.92 (4H, m,
[
a
]
D = ꢁ26 (c 0.21, DMSO); 1H NMR (DMSO-d6)
d
aromatics), 7.53 (2H, m, aromatics), 5.62 (1H, d, J1 ,2 7.9 Hz, H-10), 5.50 (1H, d, J
4.0 Hz, OH), 5.38 (1H, d, J 2.6 Hz, OH), 5.22 (1H, d, J 4.0 Hz, OH), 4.68 (1H, t, OH),
3.84–3.29 (6H, m, H-20, H-30, H-40, H-50, H-60ab); 13C NMR (DMSO-d6) d (ppm)
146.3 (triazole C-4), 133.1, 132.5, 128.5, 128.0, 127.9, 127.7, 126.6, 126.1,
123.6, 123.4, (aromatics), 120.8 (triazole C-5), 87.7 (C-10), 79.9, 76.8, 72.2, 69.6
(C-20–C-50), 60.7 (C-60). Anal. Calcd for C18H19N3O5 (357.37): C, 60.50; H, 5.36;
N, 11.76. Found: C, 60.61; H, 5.31; N, 11.82.
0
0
20. Compound 3d. 1-(b-
solid. Mp: 156–158 °C (lit.26 mp: 162–163 °C); [
21. Compound 4d. N-Acetoxyacetyl-2,3,4,6-tetra-O-acetyl-b-
amine: colourless syrup. Rf: 0.24 (1:1 EtOAc–hexane),
D
-Glucopyranosyl)-4-hydroxymethyl-1,2,3-triazole: white
D = ꢁ5 (c 0.16, H2O).
-glucopyranosyl-
D = +59 (c 0.24,
33. Oikonomakos, N. G.; Kosmopolou, M.; Zographos, S. E.; Leonidas, D. D.; Somsák,
L.; Nagy, V.; Praly, J.-P.; Docsa, T.; Tóth, B.; Gergely, P. Eur. J. Biochem. 2002, 269,
1684–1696.
34. Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.;
Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron
Lett. 1995, 36, 2145–2148.
35. Gregoriou, M.; Noble, M. E. M.; Watson, K. A.; Garman, E. F.; Krülle, T. M.;
Fuente, C.; Fleet, G. W. J.; Oikonomakos, N. G.; Johnson, L. N. Protein Sci. 1998, 7,
915–927.
a
]
D
[
a
]
CHCl3); 1H NMR (CDCl3) d (ppm) 7.05 (1H, d, J1,NH 9.2 Hz, NH), 5.33, 5.24, 5.08,
4.96 (4 ꢂ 1H, 4 pseudo t, J 9.2, 10.6 Hz in each, H-1, H-2, H-3, H-4), 4.69, 4.43
(2 ꢂ 1H, 2d, J 15.9 Hz,CH2a, CH2b), 4.33 (1H, dd, J6a,6b 13.2 Hz, H-6a), 4.09 (1H,
dd, J5,6b 2.6 Hz, H-6b), 3.86 (1H, ddd, J5,6a 5.3 Hz, H-5), 2.20, 2.09, 2.05, 2.04,
2.03 (15H, 5s, 5 ꢂ CH3); 13C NMR (CDCl3) d (ppm) 171.3, 170.5, 169.7, 169.6,
169.4, 167.9 (CO), 77.8 (C-1), 73.6, 72.3, 70.2, 68.0 (C-2–C-5), 62.4, 61.4 (C-6,
CH2), 20.6, 20.4 (4) (CH3). Anal. Calcd for C18H25NO12 (447.40): C, 48.32; H,
5.63; N, 3.13. Found: C, 48.41; H, 5.22; N, 3.02.
36. Kraulis, P. J. Appl. Crystallogr. 1991, 24, 946–950.