Communication
Organic & Biomolecular Chemistry
5 (a) O. Thomsen, Z. Immunitaetsforsch., 1927, 52, 85–90; 11 (a) S. A. Svarovsky and J. J. Barchi Jr., Carbohydr. Res., 2003,
(b) V. Friedenreich, The Thomsen hemagglutination phenom-
enon, Copenhagen, Denmark, 1930.
6 (a) S. D. Kuduk, J. B. Schwarz, X.-T. Chen, P. W. Glunz,
D. Sames, G. Ragupathi, P. O. Livingston and
S. J. Danishefsky, J. Am. Chem. Soc., 1998, 120, 12474–
338, 1925–1935; (b) D. Cato, T. Buskas and G. J. Boons,
J. Carbohydr. Chem., 2005, 24, 503–516; (c) W.-T. Jiaang,
M.-Y. Chang, P.-H. Tseng and S.-T. Chen, Tetrahedron Lett.,
2000, 41, 3127–3130; (d) S. J. Keding, A. Endo and
S. J. Danishefsky, Tetrahedron, 2003, 59, 7023–7031.
12485; (b) P. J. Sabbatini, G. Ragupathi, C. Hood, 12 E. D. Goddard-Borger and R. V. Stick, Org. Lett., 2007, 9,
C. A. Aghajanian, M. Juretzka, A. Iasonos, M. L. Hensley, 3797–3800.
M. K. Spassova, O. Ouerfelli, D. R. Spriggs, W. P. Tew, 13 L. A. Marcaurelle, Y. Shin, S. Goon and C. R. Bertozzi, Org.
J. Konner, H. Clausen, N. Abu Rustum, S. J. Dansihefsky Lett., 2001, 3, 3691–3694.
and P. O. Livingston, Clin. Cancer Res., 2007, 13, 4170– 14 S. Hosokawa, T. Ogura, H. Togashi and K. Tatsuta, Tetra-
4177; (c) J. Zhu, Q. Wan, D. Lee, G. Yang, M. K. Spassova, hedron Lett., 2005, 46, 333–337.
O. Ouerfelli, G. Ragupathi, P. Damani, P. O. Livingston and 15 D. Crich, M. de la Mora and A. U. Vinod, J. Org. Chem.,
S. J. Danishefsky, J. Am. Chem. Soc., 2009, 131, 9298–9303; 2003, 68, 8142–8148.
(d) A. Hoffmann-Röder, A. Kaiser, S. Wagner, N. Gaidzik, 16 M. Andersson and S. Oscarson, Glycoconjugate J., 1992, 9,
D. Kowalczyk, U. Westerlind, B. Gerlitzki, E. Schmitt and 122–125.
H. Kunz, Angew. Chem., Int. Ed., 2010, 49, 8498–8503; 17 A. B. Smith III and G. R. Ott, J. Am. Chem. Soc., 1996, 118,
(e) G. F. Springer, P. R. Desai, B. D. Spencer, H. Tegtmeyer, 13095–13096.
S. C. Carlstedt and E. F. Scanlon, Cancer Detect. Prev., 1995, 18 The excess TBDPSCl was hydrolyzed to TBDPSOH, regret-
19, 374–380; (f) R. P. Brinãs, A. Sundgren, P. Sahoo,
S. Morey, K. Rittenhouse-Olson, G. E. Wilding, W. Deng
and J. J. Barchi, Bioconjugate Chem., 2012, 23, 1513–1523.
7 (a) V. V. Glinsky, G. V. Glinsky, K. Rittenhouse-Olson,
M. E. Huflejt, O. V. Glinskii, S. L. Deutscher and
tably TBDPSOH and 9 had the same rf ethyl acetate–
hexanes, requiring the usage of toluene for the separation.
19 C.-C. Lin, N.-P. Lin, L. S. Sahabuddin, V. R. Reddy,
L.-D. Huang, K. C. Hwang and C.-C. Lin, J. Org. Chem.,
2010, 75, 4921–4928.
T. P. Quinn, Cancer Res., 2001, 61, 4851–4857; 20 The yield of this reaction was not calculated because of the
(b) J. M. Rhodes, B. J. Campbell and L.-G. Yu, Biochem. Soc. presence of an inseparable impurity.
Trans., 2008, 36, 1482–1486; (c) J. Heimburg, J. Yan, 21 C.-H. Wong, X.-S. Ye and Z. Zhang, J. Am. Chem. Soc., 1998,
S. Morey, O. Glinskii, V. Huxley, L. Wild, R. Klick, R. Roy, 120, 7137–7138.
V. Glinsky and K. Rittenhouse-Olson, Neoplasia, 2006, 8, 22 D. J. Lefeber, J. P. Kamerling and J. F. G. Vliegenthart, Org.
939–948. Lett., 2000, 2, 701–703.
8 (a) B. A. Cobb, Q. Wang, A. O. Tzianabos and D. L. Kasper, 23 R. R. Schmidt and J. Michel, Angew. Chem., Int. Ed., 1980,
Cell, 2004, 117, 677–687; (b) R. A. De Silva, Q. Wang, 19, 731–732.
T. Chidley, D. K. Appulage and P. R. Andreana, J. Am. Chem. 24 S. Dziadek, C. Brocke and H. Kunz, Chem.–Eur. J., 2004, 10,
Soc., 2009, 131, 9622–9623; (c) R. Silva, D. Appulage, 4150–4162.
H. Pietraszkiewicz, K. Bobbitt, J. Media, J. Shaw, 25 H. Tanaka, M. Adachi and T. Takahashi, Chem.–Eur. J.,
F. Valeriote and P. Andreana, Cancer Immunol. Immunother., 2005, 11, 849–862.
2012, 61, 581–585; (d) N. K. Surana and D. L. Kasper, 26 See ESI† Carbon NMR data for 14.
Immunol. Rev., 2012, 245, 13–26.
9 (a) S. Cao, F. D. Tropper and R. Roy, Tetrahedron, 1995, 51,
27 G. T. Hermanson, Bioconjugate Techniques, Academic Press,
San Diego, 1996.
6679–6686; (b) O. Renaudet and P. Dumy, Tetrahedron Lett., 28 O. W. Odom, D. J. Robbins, J. Lynch, D. Dottavio-Martin,
2001, 42, 7575–7578; (c) J. E. Hudak, H. H. Yu and
C. R. Bertozzi, J. Am. Chem. Soc., 2011, 133, 16127–16135.
G. Kramer and B. Hardesty, Biochemistry, 1980, 19, 5947–
5954.
10 O. Renaudet and P. Dumy, Tetrahedron Lett., 2004, 45, 29 J. Kalia and R. T. Raines, Angew. Chem., Int. Ed., 2008, 47,
65–68.
7523–7526.
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