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LETTER
Lloyd, K. O.; Danishefsky, S. J.; Livingston, P. O. Angew.
Chem., Int. Ed. Engl. 1997, 36, 125.
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References and Notes
(1) (a) Breton, C.; Šnajdrová, L.; Jeanneau, C.; Koča, J.;
Imberty, A. Glycobiology 2006, 16, 29R. (b) Paulson, J. C.;
Weinstein, J.; Schauer, A. J. Biol. Chem. 1989, 264, 10931.
(2) (a) Taniguchi, N.; Yoshimura, M.; Miyoshi, E.; Ihara, Y.;
Nishikawa, A.; Fujii, S. Glycobiology 1996, 6, 691.
(b) Hiraiwa, N.; Dohi, T.; Kawakami-Kimura, N.; Yumen,
M.; Ohmori, K.; Maeda, M.; Kannagi, R. J. Biol. Chem.
1996, 271, 31556. (c) Hakomori, S. Adv. Cancer Res. 1989,
52, 257.
(3) (a) Ohyama, C. Int. J. Clin. Oncol. 2008, 13, 308. (b) Zhao,
Y.-Y.; Takahashi, M.; Gu, J.-G.; Miyoshi, E.; Matsumoto,
A.; Kitazume, S.; Taniguchi, N. Cancer Sci. 2008, 99, 1304;
and references cited therein.
(15) Wang, L.-X.; Lee, Y. C. J. Chem. Soc., Perkin Trans. 1
1996, 581.
(16) Excoffier, G.; Gagnare, D.; Utille, J.-P. Carbohydr. Res.
1975, 39, 368.
(17) (a) Komori, T.; Kondo, S.; Ando, H.; Ishida, H.; Kiso, M.
Carbohydr. Res. 2002, 337, 1679. (b) Jain, R. K.; Matta,
K. L. Carbohydr. Res. 1990, 208, 51.
(18) Analytical Data for Compound 1
1H NMR (400 MHz, CD3OD): d = 1.97 (s, 3 H, NHCOCH3),
2.03 (s, 3 H, NHCOCH3), 3.93–3.41 (m, 16 H), 4.03–3.98
(m, 2 H), 4.11–4.09 (m, 1 H), 4.23–4.17 (m, 1 H), 4.39 (d,
J = 7.6 Hz, 1 H, H-1¢), 4.46–4.41 (m, 1 H), 4.63 (d, J = 8.4
Hz, 1 H, H-1¢¢), 5.17 (dd, 3J = 10.4 Hz, 2J = 1.6 Hz, 1 H,
OCH2CH=CHcisHtrans), 5.32 (dd, 3J = 17.2 Hz, 2J = 1.6 Hz, 1
H, OCH2CH=CHcisHtrans), 5.99–5.89 (m, 1 H,
(4) Chandrasekaran, E. V.; Xue, J.; Neelamegham, S.; Matta,
K. L. Carbohydr. Res. 2006, 341, 983.
(5) (a) Chandrasekaran, E. V.; Xue, J.; Piskorz, C.; Locke,
R. D.; Tóth, K.; Slocum, H. K.; Matta, K. L. J. Cancer Res.
Clin. Oncol. 2007, 133, 599; and references cited therein.
(b) Chandrasekaran, E. V.; Jain, R. K.; Rhodes, J. M.;
Chawda, R.; Piskorz, C.; Matta, K. L. Glycoconjugate J.
1999, 16, 523. (c) Chandrasekaran, E. V.; Jain, R. K.; Vig,
R.; Matta, K. L. Glycobiology 1997, 7, 753.
(6) (a) Campanero-Rhodes, M. A.; Childs, R. A.; Kiso, M.;
Komba, S.; Narvor, C. L.; Warren, J.; Otto, D.; Crocker,
P. R.; Feizi, T. Biochem. Biophys. Res. Commun. 2006, 292,
1141; and references cited therein. (b) Honke, K.;
Taniguchi, N. Med. Res. Rev. 2002, 22, 637. (c) Fukuda,
M.; Hiraoka, N.; Akama, T. O.; Fukuda, M. N. J. Biol.
Chem. 2001, 276, 47747.
(7) Bernstein, M. A.; Hall, J. D. Carbohydr. Res. 1980, 78, C1.
(8) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.;
Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int.
Ed. Engl. 1997, 36, 1998.
(9) Sawada, N.; Ito, M.; Ishida, H.; Kiso, M. Tetrahedron Lett.
2001, 42, 1745.
OCH2CH=CH2) ppm. 13C NMR (100 MHz, CD3OD):
d = 22.9 (COCH3), 23.2 (COCH3), 55.5, 61.8, 62.8, 62.9,
69.4, 70.3, 72.4, 72.8, 72.9, 74.7, 74.8, 75.8, 77.0, 77.9, 78.5
(C-3), 78.9 (C-3¢), 98.2, 104.6, 106.5 (C-1, C-1¢, C-1¢¢),
117.8 (CH=CH2), 135.7 (CH=CH2), 174.2 (COCH3), 175.4
(COCH3) ppm. ESI-MS: m/z calcd for C25H41N2NaO19S:
728.2; found: 751.2 [M + Na]+.
(19) (a) Kartha, K. P. R.; Jennings, H. J. J. Carbohydr. Chem.
1990, 9, 777. (b) Youssef, R. H.; Silwanis, B. A.; El-
Sokkary, R. I.; Nematalla, A. S.; Nashed, M. A. Carbohydr.
Res. 1993, 240, 287.
(20) Analytical Data for Compound 6
1H NMR (400 MHz, CD3OD): d = 2.06 (s, 3 H, NHCOCH3),
3.26 (m, 1 H), 3.91–3.46 (m, 14 H), 4.16–4.01 (m, 2 H),
4.36–4.28 (m, 4 H, H-1, J = 8.0 Hz, incorporated with other
protons), 4.44 (d, J = 7.6 Hz, 1 H, H-1¢), 4.61 (d, J = 8.4 Hz,
1 H, H-1¢¢), 5.16 (dd, 3J = 10.8 Hz, 2J = 1.2 Hz, 1 H,
OCH2CH=CHcisHtrans), 5.32 (dd, 3J = 17.6 Hz, 2J = 1.6 Hz,
1 H, OCH2CH=CHcisHtrans), 5.99–5.93 (m, 1 H,
OCH2CH=CH2) ppm. 13C NMR (100 MHz, CD3OD):
d = 23.5 (COCH3), 54.2, 61.4, 61.9, 62.7, 69.8, 70.9, 71.3,
73.8, 74.9, 75.7, 76.4, 76.6, 76.7, 76.8, 81.0 (C-3), 81.1 (C-
3¢), 103.4, 104.9, 105.0 (C-1, C-1¢, C-1¢¢), 117.6 (CH=CH2),
135.8 (CH=CH2), 174.9 (COCH3) ppm. ESI-MS: m/z calcd
for C23H38NNaO19S: 687.2; found: 710.2 [M + Na]+.
(10) Hancock, G.; Galpin, I. J. Tetrahedron Lett. 1982, 23, 249.
(11) Xia, J.; Abbas, S. A.; Locke, R. D.; Piskorz, C. F.; Alderfer,
J. L.; Matta, K. L. Tetrahedron Lett. 2000, 41, 169.
(12) (a) Sundgren, A.; Barchi, J. J. Jr. Carbohydr. Res. 2008, 343,
1594. (b) Chefalo, P.; Pan, Y.; Nagy, N.; Harding, C.; Guo,
Z. Glycoconjugate J. 2004, 20, 407. (c) Ragupathi, G.;
Park, T. K.; Zhang, S.; Kim, I. J.; Graber, L.; Adluri, S.;
Synlett 2009, No. 16, 2633–2636 © Thieme Stuttgart · New York