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4. Brigl, M.; Brenner, M. Annu. Rev. Immunol. 2004, 22, 817.
5. Kronenberg, M. Annu. Rev. Immunol. 2005, 23, 877.
6. Zhou, D.; Mattner, J.; Cantu, C., III; Schrantz, N.; Yin, N.;
Gao, Y.; Sagiv, Y.; Hudspeth, K.; Wu, Y.; Yamashita, T.;
Teneberg, S.; Wang, D.; Proia, R. L.; Levery, S. B.; Savage,
P. B.; Teyton, L.; Bendelac, A. Science 2004, 306, 1786.
7. Morita, M.; Natori, T.; Akimoto, K.; Osawa, T.; Fukus-
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1H), 4.66-4.61 (m, 2H), 4.53 (m, 1H), 4.49 (t, J = 5.8 Hz,
1H), 4.42–4.36 (m, 4H), 4.31–4.29 (m, 1H), 2.43 (t,
J = 7.4 Hz, 2H), 2.23 (m, 1H), 1.92–1.86 (m, 2H), 1.82-
1.77 (m, 2H), 1.63 (m, 1H), 1.44–1.18 (m, 66H), 0.88–0.83
(m, 6H); 13C NMR (125 MHz, pyridine-d5) d 174.56,
102.81, 77.96, 74.29, 72.88, 72.26, 71.58, 69.95, 63.94,
52.78, 38.08, 35.60, 33.40, 31.64, 31.42, 31.31, 31.27, 31.20,
31.14, 31.08, 30.89, 27.78, 27.66, 24.20, 15.54; HRMS
([M+Na]+) 880.7240 calcd. 880.7212.
8. Figueroa-Perez, S.; Schmidr, R. R. Carbohydr. Res. 2000,
328, 95.
15. Janczuk, A. J.; Zhang, W.; Andreana, P. R.; Warrick, J.;
Wang, P. G. Carbohydr. Res. 2002, 337, 1247.
9. Plettenberg, O.; Bodmer-Narkevitch, V.; Wong, C. H.
J. Org. Chem. 2002, 67, 4559.
16. Zhang, W.; Wang, J.-Q.; Li, J.; Yu, L.-B.; Wang, P. G.
J. Carbohydr. Chem. 1999, 18, 1009.
10. Song, S.; Lee, T.; Jung, S.; Kim, D. Synthesis 2004, 6, 847.
11. Alessandro, D.; Alberto, M.; Alessandro, M. J. Org.
Chem. 1999, 64, 933.
12. Shirota, O.; Nakanishi, K.; Berova, N. Tetrahedron 1999,
55, 13643.
17. Taniguchi, M.; Seino, K-i.; Nakayama, T. Nat. Immunol.
2003, 4, 1164.
18. Rai, A. N.; Basu, A. Org. Lett. 2004, 6, 2861.
19. iGb3: 1H NMR (500 MHz, pyridine-d5): d 8.31 (d,
J = 8.0 Hz, 1H), 7.53 (br, 1H), 7.32 (br, 1H), 6.98 (br,
1H), 6.66 (br, 1H), 6.58 (br, 1H), 6.52 (br, 1H), 6.42 (br,
1H), 6.38 (br, 1H), 6.36 (br, 1H), 6.09 (br, 1H), 6.01 (dd,
J = 15.5, 6.0 Hz), 5.91 (dt, J = 15.3, 6.5 Hz, 1H), 5.76 (br,
1H), 5.64 (d, J = 3.8 Hz, 1H), 5.05–5.00 (m, 2H), 4.87 (d,
J = 12 Hz, 1H), 4.81–4.75 (m, 3H), 4.72–4.69 (m, 1H), 4.65
(m, 1H), 4.56 (m, 1H), 4.54–4.49 (m, 3H), 4.47–4.39 (m,
4H), 4.32–4.29 (m, 1H), 4.24–4.20 (m, 3H), 4.15 (dd,
J = 9.5, 2.5 Hz, 1H), 4.05–4.00 (m, 2H), 3.86–3.84 (m, 1H),
2.42 (t, J = 7.0 Hz, 2H), 2.06 (q, J = 6.5 Hz, 2H), 1.82 (m,
2H), 1.39–1.21 (m, 66H), 0.87 (t, J = 6.5 Hz, 3H), 0.86 (t,
J = 7.0 Hz, 3H); 13C NMR (100 MHz, pyridine-d5): d
174.20, 133.54, 133.16, 106.37, 98.59, 83.00, 81.06, 77.58,
77.47, 77.40, 75.68, 73.74, 73.60, 72.52, 71.73, 71.40, 71.30,
66.88, 63.13, 62.92, 62.73, 55.81, 50.56, 37.85, 33.65, 33.04,
33.02, 31.40, 30.94, 30.92, 30.89, 30.81, 30.70, 30.63, 30.54,
30.51, 27.31, 23.83, 15.18; HRMS ([M+Na]+) 1186.8136,
calcd. 1186.8168.
13. b-GalCer: 1H NMR (500 MHz, pyridine-d5) d 8.49 (d,
J = 8.5 Hz, 1H), 5.14 (m, 1H), 4.89 (d, J = 7.5 Hz, 1H),
4.18 (dd, J = 10.5, 5.5 Hz, 1H), 4.53 (d, J = 2.0 Hz, 1H),
4.49–4.43 (m, 2H), 4.41 (d, J = 6.0 Hz, 1H), 4.36 (t,
J = 6.0 Hz, 1H), 4.20 (t, J = 6.4 Hz, 1H), 4.12 (dd, J = 9.4,
2.7 Hz, 1H), 4.02 (t, J = 5.8 Hz, 1H), 2.40 (t, J = 7.3 Hz,
2H), 2.20 (m, 1H), 1.93-1.89 (m, 2H), 1.81–1.76 (m, 2H),
1.67 (m, 1H), 1.43-1.14 (m, 66H), 0.88–0.83 (m, 6H); 13C
NMR (125 MHz, pyridine-d5) d 174.44, 107.22, 77.98,
76.65, 76.28, 73.62, 73.54, 71.67, 71.10, 63.23, 53.19, 37.82,
34.42, 33.05, 33.04, 31.25, 31.10, 30.94, 30.86, 30.83, 30.76,
30.68, 30.55, 27.59, 27.30, 23.86, 15.21. Data can be found
in: Morita, M.; Natori, T.; Akimoto, K.; Osawa, T.;
Fukusima, H.; Koezuka, Y. Bioorg. Med. Chem. Lett.
1995, 5, 699.
14. KRN7000: 1H NMR (500 MHz, pyridine-d5) d 8.43 (d,
J = 8.6 Hz, 1H), 5.55 (d, J = 3.5 Hz, 1H), 5.25–5.21 (m,