M. Tojino, M. Mizuno / Tetrahedron Letters 49 (2008) 5920–5923
5923
J = 11.0 Hz, 1H), 4.73 (d, J = 11.0 Hz, 1H), 4.78 (d, J = 11.0 Hz, 1H), 4.83 (d,
J = 7.6 Hz, 1H), 4.89 (d, J = 11.0 Hz, 1H), 5.00 (d, J = 7.6 Hz, 1H), 5.01 (d,
J = 11.0 Hz, 1H), 5.54 (dd, J = 7.6 Hz, 9.6 Hz, 1H), 5.65 (t, J = 9.6 Hz, 1H), 5.80 (t,
J = 9.6 Hz, 1H), 6.91 (d, J = 9.6 Hz, 2H), 7.04 (d, J = 9.6 Hz, 2H), 7.14 (d, J = 7.6 Hz,
2H), 7.21–7.38 (m, 21H), 7.43 (t, J = 7.6 Hz, 2H), 7.47–7.56 (m, 2H), 7.80 (t,
Supplementary data
Supplementary data associated with this article can be found, in
J = 7.6 Hz, 2H), 7.89 (d, J = 7.6 Hz, 2H), 8.00 (d, J = 6.9 Hz, 2H). Compound 15: 1
H
NMR (CD3Cl, 600 MHz) d: 1.97–2.07 (m, 2H), 2.15–2.27 (m, 2H), 3.42 (dd,
J = 3.2 Hz, 10.0 Hz, 1H), 3.51 (t, J = 5.8 Hz, 1H), 3.77 (dd, J = 4.5 Hz, 12.1 Hz, 1H),
3.81 (dd, J = 4.8 Hz, 11.0 Hz, 1H), 3.92 (dd, J = 6.9 Hz, 11.7 Hz, 1H), 3.90–4.18
(m, 4H), 4.42 (dd, J = 4.5 Hz, 12.1 Hz, 1H), 4.56 (d, J = 11.6 Hz, 1H), 4.58 (d,
J = 11.6 Hz, 1H), 4.64 (d, J = 10.3 Hz, 1H), 4.65 (d, J = 11.7 Hz, 1H), 4.74 (d,
J = 8.2 Hz, 1H), 4.82 (d, J = 11.0 Hz, 1H), 4.90 (d, J = 11.7 Hz, 1H), 4.96 (d,
J = 11.0 Hz, 1H), 4.98 (d, J = 7.6 Hz, 1H), 5.48 (dd, J = 8.0 Hz, 10.0 Hz, 1H), 5.66 (t,
J = 9.7 Hz, 1H), 5.80 (t, J = 9.7 Hz, 1H), 6.87 (d, J = 8.9 Hz, 2H), 7.01 (d, J = 8.9 Hz,
2H), 7.21–7.38 (m, 23H), 7.40–7.52 (m, 4H), 7.79 (t, J = 7.5 Hz, 2H), 7.81 (d,
J = 6.9 Hz, 2H), 7.87 (d, J = 6.9 Hz, 2H), 8.00 (d, J = 6.9 Hz, 2H).
References and notes
1. (a) Lam, S.; Lebl, M.; Krchnak, V. Chem. Rev. 1997, 97, 411; (b) Furka, A. In
Conbinatorial Peptide and Non Peptide Libraries; Jung, G., Ed.; VCH: Weinheim,
1996; p 111; (c) Nicolau, K. C.; Xiao, X. Y.; Parandoosh, Z.; Senyei, A.; Nova, M.
P. Angew. Chem., Int. Ed. Engl. 1995, 34, 2289.
2. (a) Curran, D. P.; Oderaotoshi, Y. Tetrahedron 2001, 57, 5243; (b) Zang, W.; Luo,
Z.; Chen, C. H.-T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443; (c) Curran, D.
P.; Zhang, Q.; Richard, C.; Lu, H.; Gudipati, V.; Wilcox, C. S. J. Am. Chem. Soc.
2006, 128, 9561.
9. The glycosylation conditions: acceptors 11 (1.0 equiv), 16 (1.0 equiv) and 17
(1.0 equiv) treated with donor 18 (6.0 equiv) in the presence of TMSOTf
(0.6 equiv) at 0 °C for 16 h.
10. Although these compounds were not separated by fluorous HPLC, usual silica
gel HPLC gave good separation. HPLC conditions: Wakosil 5SIL (4.0 Â 15 mm),
gradient 85/15 hexane/AcOEt to 80/20 hexane/AcOEt. UV detection at 280 nm;
flow rate 1.0 mL/min.
3. Varki, A. Glycobiology 2006, 3, 97.
4. (a) Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozumi, Y.; Sekanina, K.; Horan, N.;
Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.; Still, W. C.; Kahone, D.
Science 1996, 274, 1520; (b) Boons, G.-J.; Heskamp, B.; Hount, F. Angew. Chem.,
Int. Ed. 1996, 35, 2079; (c) Izumi, M.; Ichikawa, Y. Tetrahedron Lett. 1998, 39,
2079; (d) Kanie, O.; Ohtsuka, I.; Ako, T.; Daikoku, S.; Kanie, Y.; Kato, R. Angew.
Chem., Int. Ed. 2006, 35, 3851.
5. (a) Fukuyama, T.; Laird, A. A.; Hotchkiss, M. Tetrahedron Lett. 1985, 26, 6291; (b)
Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389.
6. Jacob, P., III; Callery, P. S.; Shulgin, A. T.; Castagnoli, N., Jr. J. Org. Chem. 1976, 41,
3627.
7. These compounds were prepared as described in Supplementary data.
8. Compound 13: 1H NMR (CD3Cl, 600 MHz) d: 2.02–2.06 (m, 2H), 2.23–2.32 (m,
2H), 3.80–3.91 (m, 4H), 3.94–4.00 (m, 3H), 4.04–4.09 (m, 1H), 4.11 (d,
J = 9.6 Hz, 1H), 4.36–4.42 (m, 2H), 4.54–4.59 (m, 3H), 4.55 (d, J = 11.0 Hz, 1H),
4.69 (q, J = 11.7 Hz, 1H), 4.88 (d, J = 8.3 Hz, 1H), 5.37–5.39 (m, 1H), 5.56 (dd,
J = 8.3 Hz, 9.6 Hz, 1H), 5.61 (t, J = 9.6 Hz, 1H), 5.80 (t, J = 9.7 Hz, 1H), 6.79 (d,
J = 8.9 Hz, 2H), 6.91 (d, J = 9.7 Hz, 2H), 7.14 (d, J = 6.2 Hz, 2H), 7.21–7.35 (m,
21H), 7.36–7.43 (m, 2H), 7.44–7.49 (m, 2H), 7.81 (t, J = 6.9 Hz, 4H), 7.88 (d,
J = 6.9 Hz, 2H), 7.98 (d, J = 6.9 Hz, 2H). Compound 14: 1H NMR (CD3Cl,
600 MHz) d: 1.98–2.01 (m, 2H), 2.16–2.28 (m, 2H), 3.38–3.42 (m, 1H), 3.53–
3.58 (m, 1H), 3.58–3.62 (m, 2H), 3.84 (dd, J = 6.2 Hz, 11.7 Hz, 1H), 3.93–4.01 (m,
2H), 4.01–4.15 (m, 1H), 4.11 (d, J = 10.3 Hz, 1H), 4.45 (dd, J = 7.6 Hz, 11.7 Hz,
1H), 4.47 (d, J = 12.4 Hz, 1H), 4.60 (dd, J = 3.5 Hz, 12.4 Hz, 1H), 4.68 (d,
11. The glycosylation conditions: acceptors 11 (48 mg, 48
46 mol) and 17 (44 mg, 49 mol) treated with donors 18 (52 mg, 10.8
mol) in the presence of TMSOTf (3.5 L, 20
mol) at À10 °C
l
mol), 16 (37 mg,
l
l
lmol)
and 22 (85 mg, 98
l
l
l
for 14 h.
12. This reaction mixture (255 mg) was obtained. An aliquot of the reaction
mixture (189 mg) was separated over fluorous HPLC: peak 1 (compound 26,
trace), peak 2 (compound 19, 12 mg), peak 3 (compound 20, 6 mg), peak 4
(compound 23, 16 mg), peak 5 (compound 11, 5 mg), peak 6 (compound 21,
2 mg), peak 7 (compound 24, 22 mg) and peak 8 (compound 25, 27 mg).
13. This compound was characterized as shown in the following:
O
C3F7
O
OBn
O
O
BzO
CCl3
N
H
OBz
26