402
Y. Chong, C.K. Chu / Carbohydrate Research 337 (2002) 397–402
4. (a) Chang, C.-N.; Doong, S.-L.; Zhou, J. H.; Beach, J.
W.; Jeong, L. S.; Chu, C. K.; Tsai, C.-H.; Cheng, Y.-C.
J. Biol. Chem. 1992, 267, 13938–13942;
material (the major double-bond isomer, 356 mg, 0.80
mmol, 46% yield): For compound 4j [h]2D5 95.5° (c 3.6,
1
CHCl3); H NMR (CDCl3) l 7.99 (d, J 8.3 Hz, 2 H),
(b) Chang, C.-N.; Skalski, V.; Zhou, J. H.; Cheng, Y.-C.
J. Biol. Chem. 1992, 267, 22414–22420;
(c) Beach, J. W.; Jeong, L. S.; Alves, A. J.; Pohl, D.;
Kim, H. O.; Chang, C.-N.; Doong, S.-L.; Schinazi, R. F.;
Cheng, Y.-C.; Chu, C. K. J. Org. Chem. 1992, 57,
2217–2219.
7.61–7.50 (m, 5 H), 7.45 (d, J 8.3 Hz, 2 H), 6.79 (s, 1
H), 5.00 (d, J 11.8 Hz, 1 H), 4.89 (d, J 6.9 Hz, 1 H),
4.72 (d, J 11.8 Hz, 1 H), 4.63 (dd, J 7.2, 3.3 Hz, 1 H),
4.37 (dt, J 7.2, 2.7 Hz, 1 H), 4.17 (br, 1 H), 3.89 (dd, J
12.8, 2.9 Hz, 1 H), 3.79 (dd, J 12.8, 2.6 Hz, 1 H), 3.03
(br, 1 H), 2.62 (s, 3 H), 1.63 (s, 3 H), 1.50 (s, 3 H); 13C
NMR (CDCl3) l 143.95, 137.08, 134.76, 129.49, 128.52,
128.23, 127.91, 109.70, 98.73, 72.80, 71.91, 69.33, 62.32,
58.27, 26.35, 24.94, 21.52; HRFABMS (m/z) Found:
449.1764, Calcd for C22H29N2O6S: 449.1746 [M+H]+.
Anal. Calcd for C22H28N2O6S: C, 58.91; H, 6.29; N,
6.25. Found: C, 59.17; H, 6.39; N, 6.22. For the recov-
5. (a) Kim, H. O.; Ahn, S. K.; Alves, A. J.; Beach, J. W.;
Jeong, L. S.; Choi, B. G.; Van Roey, P.; Schinazi, R. F.;
Chu, C. K. J. Med. Chem. 1992, 35, 1987–1995;
(b) Hoong, L. K.; Strange, L. E.; Liotta, D. C.; Kosza-
lka, G. W.; Burns, C. L.; Schinazi, R. F. J. Org. Chem.
1992, 57, 5563–5565;
(c) Schinazi, R. F.; McMillan, A.; Cannon, D.; Mathis,
R.; Lloyd, R. M.; Peck, A.; Sommadossi, J.-P.; St. Clair,
M.; Wilson, J.; Furman, P. A.; Painter, G.; Choi, W. B.;
Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36,
2423–2431;
(d) Furman, P. A.; Davis, M.; Liotta, D. C.; Paff,
M.; Frick, L. W.; Nelson, D. J.; Dornsife, R. E.;
Wurster, J. A.; Wilson, L. J.; Fyfe, J. A.; Tuttle, J. V.;
Miller, W. H.; Condreay, L.; Averett, D. R.; Schinazi, R.
F.; Painter, G. R. Antimicrob. Agents Chemother. 1992, 3,
2686–2692.
1
ered starting material: [h]2D6 199.7° (c 4.5, CHCl3); H
NMR (CDCl3) l 9.87 (s, 1 H), 7.72 (d, J 8.3 Hz, 2 H),
7.29–7.19 (m, 7 H), 5.06 (s, 1 H), 4.83 (d, J 5.6 Hz, 1
H), 4.58 (d, J 11.5 Hz, 1 H), 4.46 (d, J 11.5 Hz, 1 H),
4.15 (d, J 5.5 Hz, 1 H), 4.05 (m, 1 H), 3.90 (d, J 13.4
Hz, 1 H), 2.33 (s, 3 H), 1.26 (s, 3 H), 0.99 (s, 3 H); 13C
NMR (CDCl3) l 145.09, 144.03, 136.58, 135.49, 129.46,
128.38, 127.93, 127.89, 127.66, 110.51, 98.14, 73.72,
71.28, 69.35, 57.44, 26.30, 25.87, 21.47
6. (a) Mansuri, M. M.; Farina, V.; Starrett, J. E., Jr.;
Benigni, D. A.; Brankovan, V.; Martin, J. C. Bioorg.
Med. Chem. Lett. 1991, 1, 65–68;
(b) Lin, T. S.; Luo, M. Z.; Liu, M. C.; Pai, S. B.;
Dutschman, G. E.; Cheng, Y.-C. J. Med. Chem. 1994, 37,
798–803;
(c) Gosselin, G.; Schinazi, R. F.; Sommadossi, J.-P.;
Mathe, C.; Bergogne, M.-C.; Aubertin, A.-M.; Kirn, A.;
Imbach, J.-L. Antimicrob. Agents Chemother. 1994, 38,
1292–1297;
(d) Bolon, P. J.; Wang, P. Y.; Chu, C. K.; Gosselin, G.;
Boudou, V.; Pierra, C.; Mathe, C.; Imbach, J.-L.; Faraj,
A.; Alaoui, M. A.; Sommadossi, J.-C.; Pai, S. B.; Zhu,
Y.-L.; Lin, J.-S.; Cheng, Y.-C.; Schinazi, R. F. Bioorg.
Med. Chem. Lett. 1996, 6, 1657–1662.
Acknowledgements
This research was supported in part by the US Public
Health Service Research Grant AI 32351 from the
National Institute of Allergy and Infectious Diseases,
NIH. We thank Dr Michael Bartlett of the College of
Pharmacy, The University of Georgia, for performing
the high-resolution mass spectra.
7. (a) Deriaz, R. E.; Overend, W. G.; Stacey, M.; Teece, E.
G.; Wiggins, L. F. J. Chem. Soc. 1949, 1879–1883;
(b) Urata, H.; Ogura, E.; Shinohara, K.; Ueda,
Y.; Akagi, M. J. Nucleic Acids Res. 1992, 20, 3325–
3332;
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