R. Rajaganesh et al. / Carbohydrate Research 346 (2011) 2327–2336
2335
(0.266 g, 1.0 mmol) product isolated as a white solid; (0.435 g,
75%); mp: 120–122 °C; 1H NMR (300 MHz, CDCl3); dH 8.66 (s,
1H), 8.55 (s, 1H), 7.73–7.83 (m, 1H), 7.18–7.45 (m, 1H), 5.14–
5.22 (m, 1H), 4.89–4.99 (m, 2H), 4.74–4.76 (m, 1H), 4.34 (m, 1H),
4.11–4.17 (m, 1H), 3.38–3.47 (m, 3H), 2.08 (s, 3H), 2.06 (s, 3H),
2.05 (s, 3H). 13C NMR (75 MHz, CDCl3) dC 170.0, 169.8, 169.4,
155.7, 155.0, 151.3, 145.8, 135.6, 130.1, 125.0, 123.7, 121.3,
118.0, 113.7, 99.6, 71.2, 70.4, 69.3, 68.8, 61.9, 20.7 (3C). Anal. Calcd
for C23H22BrN3O10: C, 47.60; H, 3.82; N, 7.24. Found: C, 47.82; H,
3.62; N, 7.07.
2.04 (s, 3H). 13C NMR (75 MHz, CDCl3) dC 167.7, 167.5, 167.2,
159.6, 152.3, 141.6, 132.1, 127.9, 121.6, 116.9, 112.5, 108.3,
100.6, 95.7, 72.8, 68.7, 68.2, 66.9, 66.3, 66.3, 18.2 (3C). Anal. Calcd
for C23H23N3O11: C, 53.39; H, 4.48; N, 8.12. Found: C, 53.50; H,
4.28; N, 8.03.
Acknowledgments
T.M. acknowledges financial support from the CSIR, New Delhi.
We also acknowledge Dr. C. P. Rao Department of Chemistry, IIT
Bombay, Mumbai for elemental analysis. We also thank DST,
New Delhi for 300 MHz NMR spectrometer under FIST scheme to
the Department of Organic Chemistry, University of Madras,
Chennai.
3.6.9. 7-Hydroxy-3-((4-methyl (2,3-di-O-acetyl-4,6-O-butyli-
dene-b-
D-glucopyranosyl))-1,2,3-triazolyl)-chromen-2-one (6i)
From 2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-b-
D
-glu-
copyranose (4a) (0.372 g, 1.0 mmol), 3-azido-7-hydroxy-chro-
men-2-one (5c) (0.204 g 1.0 mmol) product isolated as a white
solid; (0.458 g, 82%); mp: 192–194 °C; 1H NMR (300 MHz, CDCl3);
dH 8.58 (s, 1H), 8.49 (s, 1H), 7.50–7.54 (m, 1H), 6.94 (m, 2H), 5.21
(t, J = 9.3 Hz, 1H), 4.87–5.03 (m, 2H), 4.70–4.73 (m, 1H), 4.45–4.53
(m, 2H), 4.23–4.26 (m, 2H), 3.37–3.62 (m, 3H), 2.06 (s, 6H), 1.57–
1.62 (m, 2H), 1.25–1.41 (m, 2H), 0.90 (t, J = 7.2 Hz, 3H). 13C NMR
(CDCl3, 75 MHz); dC 170.4 , 170.1, 162.1, 156.3, 154.8, 144.0,
133.5, 130.4, 124.0, 119.4, 115.0, 110.8, 103.1, 102.6, 100.1, 72.1,
71.8, 68.7, 68.0, 66.6, 62.4, 36.0, 20.7 (2C), 17.4, 13.8. Anal. Calcd
for C26H29N3O11: C, 55.81; H, 5.22; N, 7.51. Found: C, 55.93; H,
5.10; N, 7.32.
Supplementary data
Supplementary data (copy of all the spectra, optimized geome-
try files and molecular orbitals) associated with this article can be
References
1. Yee, D. J.; Balsanek, V.; Sames, D. J. Am. Chem. Soc. 2004, 126, 2282–2283.
2. Beatty, K. E.; Xie, F.; Wang, Q.; Tirrell, D. A. J. Am. Chem. Soc. 2005, 127, 14150–
14151.
3. Lutz, J. F.; Zarafshani, Z. Adv. Drug Deliv. Rev. 2008, 60, 958–970.
4. Lutz, J. F. Angew. Chem., Int. Ed. 2007, 46, 1018–1025.
5. Nandivada, H.; Jiang, X. W.; Lahann, J. Adv. Mater. 2007, 19, 2197–2208.
6. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057–3064.
7. Singh, N. S.; Pandey, K.; Tripathi, R. P. Carbohydr. Res. 2010, 345, 1641–1648.
8. Robtovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed.
2002, 41, 2596–2599.
9. Karthik Kumar, K.; Mahesh Kumar, R.; Subramanian, V.; Mohan Das, T.
Carbohydr. Res. 2010, 345, 2297–2304.
10. Droumagueta, C. L.; Wang, C.; Wang, Q. Chem. Soc. Rev. 2010, 39, 1233–
1239.
11. Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett.
2004, 6, 4603–4606.
12. Zhou, Z.; Fahrni, C. J. J. Am. Chem. Soc. 2004, 126, 8862–8863.
13. Tripathi, R. P.; Yadav, A. K.; Ajay, A.; Bisht, S. S.; Chaturvedi, V.; Sinha, K. Eur. J.
Med. Chem. 2010, 45, 142–148.
14. Schiedel, M. S.; Briehn, C. A.; Bauerle, P. Angew. Chem., Int. Ed. 2001, 40, 4677–
4680.
15. Wang, S.; Chang, Y. T. J. Am. Chem. Soc. 2006, 128, 10380–10381.
16. Ahn, Y. H.; Lee, J. S.; Chang, Y. T. J. Am. Chem. Soc. 2007, 129, 4510–4511.
17. Rosania, G. R.; Lee, J. W.; Ding, L.; Yoon, H. S.; Chang, Y. T. J. Am. Chem. Soc. 2003,
125, 1130–1131.
18. Li, Q.; Lee, J. S.; Ha, C.; Park, C. B.; Yang, G.; Gan, W. B.; Chang, Y. T. Angew.
Chem., Int. Ed. 2004, 43, 6331–6335.
19. Xie, F.; Sivakumar, K.; Zeng, Q.; Bruckman, M. A.; Hodges, B.; Wang, Q.
Tetrahedron 2008, 64, 2906–2914.
3.6.10. 7-Hydroxy-3-((4-methyl (2,3-di-O-acetyl-4,6-O-ethyl-
idene-b-
D
-glucopyranosyl))-1,2,3-triazolyl)-chromen-2-one (6j)
-glu-
From 2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-ethylidene-b-
D
copyranose (4b) (0.334 g, 1.0 mmol), 3-azido-7-hydroxy-chro-
men-2-one (5c) (0.204 g 1.0 mmol) product isolated as a pale
yellow solid; (0.419 g, 79%); mp: 158–160 °C 1H NMR (300 MHz,
CDCl3); dH 8.57 (s, 1H), 8.49 (s, 1H), 7.51–7.54 (m, 2H), 6.94 (m,
2H), 5.21 (t, J = 9.0 Hz, 1H), 4.88–5.04 (m, 2H), 4.69–4.73 (m, 2H),
4.22–4.27 (m, 1H), 3.45–3.64 (m, 4H), 2.0 (s, 6H), 1.33 (d,
J = 4.8 Hz, 3H). 13C NMR (75 MHz, CDCl3) dC 170.4, 170.1, 161.9,
156.1, 154.7, 144.0, 134.3, 130.4, 124.0, 122.9, 114.9, 110.9,
103.1, 100.1, 99.7, 77.8, 72.2, 71.9, 68.0, 66.4, 62.4, 20.8, 20.7,
20.2. Anal. Calcd for C24H25N3O11: C, 54.24; H, 4.74; N, 7.91. Found:
C, 54.45; H, 4.45; N, 7.60.
3.6.11. 7-Hydroxy-3-((4-methyl (2,3,4-tri-O-acetyl-b-D-gluco-
yr-anosyl))-1,2,3-triazolyl)-chromen-2-one (6k)
From 2-propyn-1-yl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranose
(4c) (0.386 g, 1.0 mmol), 3-azido-7-hydroxy-chromen-2-one (5c)
(0.204 g 1.0 mmol) product isolated as a white solid; (0.477 g,
81%); mp: 182–184 °C 1H NMR (300 MHz, CDCl3); dH 8.58 (s, 1H),
8.49 (s, 1H), 7.54 (d, J = 9.3 Hz, 2H), 6.93 (m, 2H), 5.06–5.25 (m,
4H), 5.02–5.03 (m, 1H), 4.69–4.72 (m, 1H), 4.17–4.33 (m, 2H),
3.76–3.79 (m, 1H), 2.13 (s, 3H), 2.06 (s, 3H), 2.04 (s, 3H), 2.01 (s,
3H). 13C NMR (CDCl3, 75 MHz); dC 171.0, 170.4, 169.5, 169.4,
155.7, 154.7, 134.4, 133.0, 130.4, 125.6, 124.2, 122.9, 114.9,
113.0, 103.2, 99.6, 72.8, 72.0, 71.3, 68.3, 62.3, 61.9, 20.8 (2C),
20.7, 20.6. Anal. Calcd for C26H27N3O13: C, 52.97; H, 4.62; N, 7.13.
Found: C, 52.87; H, 4.42; N, 6.99.
20. Chang, K. C.; Su, I.; Senthilvelan, A.; Chung, W. Org. Lett. 2007, 9, 3363–3366.
21. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev. 2004, 104, 3059–
3078.
22. Jones, G.; Rahman, M. A. J. Phys. Chem. 1994, 98, 13028–13037.
23. Hoshiyama, M.; Kubo, K.; Igarashi, T.; Sakurai, T. J. Photochem. Photobiol. A:
Chem. 2001, 138, 227–233.
24. McAdam, C. J.; Morgan, J. L.; Murray, R. E.; Robinson, B. H. L.; Simpson, J. Aust. J.
Chem. 2004, 57, 525–530.
25. Wu, J. S.; Liu, W. M.; Zhuang, X. Q.; Wang, F.; Wang, P. F.; Tao, S. L.; Zhang, X. H.;
Wu, S. K.; Lee, S. T. Org. Lett. 2007, 9, 33–36.
26. Li, X.; Zhang, G.; Ma, H.; Zhang, D.; Li, J.; Zhu, D. J. Am. Chem. Soc. 2004, 126,
11543–11548.
27. Harris, R. F.; Nation, A. J.; Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122,
11270–11271.
28. Magri, D. C.; Brown, G. J.; Mcclean, G. D.; De silva, A. P. J. Am. Chem. Soc. 2006,
128, 4950–4951.
29. Yang, W.; Fan, H.; Gao, X.; Gao, S.; Karnati, V.; Ni, W.; Hooks, W.; Carson, J.;
Weston, B.; Wang, B. Chem. Biol. 2004, 11, 439–448.
3.6.12. 7-Hydroxy-3-((4-methyl (2,3,4-tri-O-acetyl-b-D-xylopyr-
anosyl))-1,2,3-triazolyl)-chromen-2-one (6l)
30. Varski, A. Glycobiology 1993, 3, 97–130.
From 2-propyn-1-yl 2,3,4-tri-O-acetyl-b-D-xylopyranose (4d)
31. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2355–2359.
32. White, M. A.; Leblanc, M. J. Chem. Educ. 1999, 76, 1201–1205.
33. Westlund, R.; Glimsdal, E.; Lindgren, M.; Vestberg, R.; Hawker, C.; Lopes, C.;
Malmstrom, E. J. Mater. Chem. 2008, 18, 166–175.
34. Lcli, S.; Astley, A. S.; Timur, C.; Anac, O.; Sezer, O.; Dabak, K. J. Lumin. 1999, 82,
41–48.
(0.314 g, 1.0 mmol), 3-azido-7-hydroxy-chromen-2-one (5c)
(0.204 g 1.0 mmol) product isolated as a white solid; (0.439 g,
85%); mp: 130–132 °C 1H NMR (300 MHz, CDCl3); dH 8.58 (s, 1H),
8.49 (s, 1H), 7.51–754 (m, 1H), 6.93–6.95 (m, 2H), 5.15–5.23 (m,
1H), 4.89–5.03 (m, 3H), 4.67–4.84 (m, 2H), 4.34–35 (m, 1H),
4.11–4.21 (m, 1H), 3.38–3.48 (m, 1H), 2.08 (s, 3H), 2.06 (s, 3H),
35. Sears, P.; Wong, C. H. Cell. Mol. Life Sci. 1998, 54, 223–252.
36. Johnsson, N.; Johnsson, K. Chembiochem 2003, 4, 803–812.