Z. Li et al. / Tetrahedron Letters 49 (2008) 7243–7245
7245
Table 2
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Synthesis of glycosylated flavonols
Flavonol
Donor (5)
Yield (%) (6)
Yield (%) (7)
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P.; Chen, L.; Shen, Y.; Luo, M.; Zuo, G.; Hu, J.; Duan, D.; Nie, Y.; Shi, X.; Wang, W.;
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D. A. Cancer Res. 2005, 65, 1027–1034.
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2007, 15, 5018–5034.
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14. Maloney, D. J.; Hecht, S. M. Org. Lett. 2005, 7, 1097–1099.
15. Oyama, K.-i.; Kawaguchi, S.; Yoshida, K.; Kondo, T. Tetrahedron Lett. 2007, 48,
6005–6009.
16. Urgaonkar, S.; Shaw, J. T. J. Org. Chem. 2007, 72, 4582–4585.
17. Algar, J.; Flynn, J. P. Proc. Roy. Irish. Acad. 1934, 42B, 1–8.
18. Oyamada, T. J. Chem. Soc. Jpn. 1934, 55, 1256.
4a
4a
4a
4a
4j
4j
4j
4j
4l
4l
4l
4l
4o
4o
4o
4o
Glucose (5a)
Galactose (5b)
Xylose (5c)
Arabinose (5d)
Glucose (5a)
Galactose (5b)
Xylose (5c)
Arabinose (5d)
Glucose (5a)
Galactose (5b)
Xylose (5c)
Arabinose (5d)
Glucose (5a)
Galactose (5b)
Xylose (5c)
63 6aa
69 6ab
54 6ac
85 6ad
57 6ja
44 6jb
26 6jc
59 6jd
77 6la
56 6lb
42 6lc
50 6ld
65 6oa
56 6ob
24 6oc
34 6od
95 7aa
85 7ab
92 7ac
93 7ad
95 7ja
90 7jb
90 7jc
92 7jd
79 7la
94 7lb
99 7lc
93 7ld
85 7oa
86 7ob
99 7oc
81 7od
Arabinose (5d)
19. Qin, C. X.; Chen, X.; Hughes, R. A.; Williams, S. J.; Woodman, O. L. J. Med. Chem.
2008, 51, 1874–1884.
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Berghe, D. A.; Vlietinck, A. J. J. Med. Chem. 1991, 34, 736–746.
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Library; Boldi, A. M., Ed.; CRC Press: New York, 2006; pp 209–226.
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Cardellina, I. J. H.; Boyd, M. R. J. Med. Chem. 1998, 41, 2333–2338.
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protocol gave decent yield of desired products. This general proce-
dure can be used to make more glycosylated flavonols with poten-
tial biological activities.
Acknowledgment
24. van Acker, F. A. A.; Hageman, J. A.; Haenen, G. R. M. M.; van der Vijgh, W. J. F.;
Bast, A.; Menge, W. M. P. B. J. Med. Chem. 2000, 43, 3752–3760.
25. Du, Y.; Wei, G.; Linhardt, R. J. Tetrahedron Lett. 2003, 44, 6887–6890.
26. Spectroscopic data for respresentative library members: Compound 6ab: H NMR
(CDCl3): d 8.16 (dd, J = 7.2, 1.4 Hz, 1H), 7.95 (d, J = 1.8 Hz, 1H), 7.69–7.62 (m,
2H), 7.48 (d, J = 7.2 Hz, 1H), 7.37 (t, J = 7.2 Hz, 1H), 6.95 (d, J = 7.2 Hz, 1H), 5.72
(d, J = 7.9 Hz, 1H), 5.40 (dd, J = 10.8, 7.2 Hz, 1H), 5.38 (d, J = 3.6 Hz, 1H), 5.13
(dd, J = 10.8, 3.6 Hz, 1H), 4.03 (s, 3H), 3.95 (s, 3H), 3.88–3.87 (m, 3H), 2.14 (s,
3H), 2.11 (s, 3H), 1.97 (s, 3H), 1.86 (s, 3H). Compound 7ab: H NMR (DMSO-d6):
d 8.10 (dd, J = 1.7, 8.1 Hz, 1H), 8.05 (d, J = 1.7 Hz, 1H), 7.83 (dt, J = 7.7, 15.4 Hz,
1H), 7.76 (d, J = 8.5 Hz, 1H), 7.69 (dd, J = 2.1, 8.5 Hz, 1H), 7.50 (dt, J = 0.9, 7.3 Hz,
1H), 7.12 (d, J = 8.5 Hz, 1H), 5.60 (d, J = 8.1 Hz, 1H), 5.22 (d, J = 4.2 Hz, 1H), 4.87
(d, J = 5.6 Hz, 1H), 4.52 (d, J = 3.8 Hz, 1H), 4.45 (t, J = 5.1 Hz, 1H), 3.85 (s, 6H),
3.68 (t, J = 3.4 Hz, 1H), 3.58 (m, 1H), 3.44 (m, 2H), 3.36 (d, J = 3.8 Hz, 1H), 3.17
(d, J = 5.5 Hz, 1H).
We thank Binghamton University Research Foundation for the
financial support of the research.
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