J = 7.6 Hz, 2H), 3.20 (t, J = 7.6 Hz, 2H), 2.60 (s, 4H), 1.54–1.51 (m,
4H), 1.43–1.40 (m, 4H), 1.40–1.20 (m, 40H), 0.86–0.83 (m, 6H). 13C
NMR (100 MHz, DMSO-d6): d 170.9, 170.4, 165.7, 165.6, 165.0,
139.6, 139.4, 139.3, 139.2, 135.7, 135.4, 135.2, 130.6, 128.6(d),
127.0, 123.2, 122.6, 121.9, 121.7, 119.9, 118.4, 116.1, 116.0, 112.8,
47.0, 45.1, 31.6, 31.2, 28.7(d), 28.6, 28.5, 27.3 (d), 26.4, 26.3,
22.0, 13.9. MS (ESI) m/z: 1492.8 [M + Na]+. HRMS (MALDI-
TOF): Calcd. for C88H112N10NaO10 [M + Na]+: 1491.8461. Found:
1491.8450.
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To a stirred solution of benzene-1,3-dicarboxylic acid (0.17 g, 1.0
mmol) in methanol (5 mL) was added aqueous tetrabutylam-
monium hydroxide solution (5 mL, 25%). The reaction mixture
was stirred at room temperature overnight. After removal of the
solvent, the resulting residue was dried under vacuum at 80 ◦C to
give 11 quantitatively as a sticky white solid. 1H NMR (400 MHz,
DMSO-d6): d 8.25 (s, 1H), 7.64 (d, J = 7.6 Hz, 2H), 7.00 (t, J =
7.6 Hz, 1H), 3.17 (t, J = 8.0 Hz, 16H), 1.55 (m, 16H),1.35–1.27
(m, 16H), 0.93 (t, J = 7.2 Hz, 24H).
Compound 12 was prepared from the reaction of benzoic acid
and tetrabutylammonium hydroxide according to a procedure
similar to that described for compound 11. 1H NMR (400 MHz,
DMSO-d6): d 7.79 (m, 2H), 7.20 (m, 3H), 3.17 (t, J = 8.0 Hz, 16H),
1.55 (m, 16H),1.35–1.27 (m, 16H), 0.93 (t, J = 7.2 Hz, 24H).
Compound 13 was prepared from the reaction of cis,cis-1,3,5-
cyclohexanetricarboxylic acid and tetrabutylammonium hydrox-
ide according to a procedure similar to that described for
compound 11.
1H NMR (400 MHz, DMSO-d6): d 3.18 (t, J = 8.4 Hz, 24H),
1.69 (m, 3H), 1.57 (m, 27H),1.35–1.27 (m, 24H), 1.01 (m, 3H),
0.93 (t, J = 7.2 Hz, 36H).
Compound 14 was prepared from the reaction of benzene-1,4-
dicarboxylic acid and tetrabutylammonium hydroxide according
to a procedure similar to that described for compound 11.
1H NMR (400 MHz, DMSO-d6): d 7.61 (s, 4H), 3.17 (t, J =
8.0 Hz, 16H), 1.55 (m, 16H),1.35–1.27 (m, 16H), 0.93 (t, J =
7.2 Hz, 24H).
Compound 15 was prepared from the reaction of benzene-1,2-
dicarboxylic acid and tetrabutylammonium hydroxide according
to a procedure similar to that described for compound 11.
1H NMR (400 MHz, DMSO-d6): d 7.06 (m, 2H), 6.80 (m, 2H),
3.17 (t, J = 8.0 Hz, 16H), 1.55 (m, 16H),1.35–1.27 (m, 16H), 0.93
(t, J = 7.2 Hz, 24H).
Compounds L-16 and D-16 were prepared from the reaction of
L-glumatic acid and D-glumatic acid and tetrabutylammonium
hydroxide according to a procedure similar to that described
for compound 11, respectively. 1H NMR (400 MHz, DMSO-
d6): d 3.17 (t, J = 8.0 Hz, 16H), 1.99 (m, 1H), 1.86 (m, 1H),
1.74 (m, 1H), 1.55 (m, 16H),1.35–1.27 (m, 17H), 0.93 (t, J =
7.2 Hz, 24H).
Acknowledgements
9 (a) L. Fischer, P. Claudon, N. Pendem, E. Miclet, C. Didierjean, E.
Ennifar and G. Guichard, Angew. Chem., Int. Ed., 2010, 49, 1067–1070;
(b) L. Fischer, C. Didierjean, F. Jolibois, V. Semetey, J. M. Lozano, J.-P.
Briand, M. Marraud, R. Poteau and G. Guichard, Org. Biomol. Chem.,
2008, 6, 2596–2610; (c) A. Violette, M. C. Averlant-Petit, V. Semetey,
We thank MOST (2007CB808001), NSFC (20732007, 20921091,
20872167, 20974118, 20972180), and STCSM (09XD1405300,
10PJ1412200) for financial support.
8128 | Org. Biomol. Chem., 2011, 9, 8122–8129
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