346
P. Steunenberg et al. / Tetrahedron: Asymmetry 16 (2005)337–346
Elliott, T.;Cresswell, P.;Wilson, I. A.;Dwek, R. A.
20, 362;Lo-Man, R.;Bay, S.;Vichier-Guerre, S.;Deriaud,
E.;Cantacuzene, D.;Leclerc, C. Cancer Res. 1999, 59,
1520;Allen, J. R.;Danishefsky, S. J. J. Am. Chem. Soc.
1999, 121, 10875;Kuberan, B.;Linhardt, R. J. Curr. Org.
Chem. 2000, 4, 653;, See also: Bousquet, E.;Spadaro, A.;
Pappalardo, M. S.;Bernardini, R.;Romeo, R.;Panza, L.;
Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527.
4. (a) Babirad, S. A.;Wang, Y. J. Org. Chem. 1987, 52, 1370;
(b) Babirad, S. A.;Wang, Y.;Kishi, Y.;Goekjian, P. G. J.
Org. Chem. 1987, 52, 4825.
5. (a) Schmidt, R. R.;Preuss, R. Tetrahedron Lett. 1989, 30,
3409;(b) Preuss, R.;Schmidt, R. R. J. Carbohydr. Chem.
1991, 10, 887;(c) Wang, Y.;Babirad, S. A.;Kishi, Y. J.
Org. Chem. 1992, 57, 468;(d) Bimwala, R. R.;Vogel, P. J.
Org. Chem. 1992, 57, 2076;(e) Preuss, R.;Jung, K. H.;
Schmidt, R. R. Liebigs Ann. Chem. 1992, 377;(f) Xin, Y.
Science 2001, 291, 2370;(c) Glycosciences: Status and
Perspectives;Gabius, H.-J., Gabius, S., Eds.;Chapmann
& Hall: London, UK, 1997;(d) Sears, P.;Wong, C.-H.
Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 12086;(e)
Kiessling, L. L.;Pohl, N. L. Chem. Biol. 1996, 3, 71;(f)
Beuth, J.;Ko, H. L.;Pulverer, G.;Uhlenbruck, G.;
Pichlmaier, H. Glycoconjugate J. 1995, 12, 1;(g) Lasky, L.
A. Annu. Rev. Biochem. 1995, 64, 113;(h) Toyokuni, T.;
Singhal, A. K. Chem. Soc. Rev. 1995, 24, 231;(i) Varki, A.
Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7390;(j) Feizi, T.
Curr. Opin. Struct. Biol. 1993, 3, 701;(k) Hakomori, S.
Curr. Opin. Immunol. 1991, 3, 646;(l) Wharton, S. A.;
Weis, W.;Skehel, J. J.;Wiley, D. C. The Infuenza Virus;
Plenum: New York, 1989;Alper, J. Science 2001, 291,
2339;Bols, M. Acc. Chem. Res. 1998, 31, 1;Barchi, J. J.,
Jr. Curr. Pharm. Des. 2000, 6, 485;Musser, J. H.;
Anderson, M. B.;Fugedi, P. Pharm. News 1996, 3, 11;
Mulligan, M. S.;Paulson, J. C.;DeFrees, S.;Zheng, Z. L.;
C.;Mallet, J. M.;Sinay , P. J. Am. Chem. Soc. 1993, 864;
¨
(g) Vauzeilles, B.;Cravo, P.;Mallet, J. M.;Sinay
Synlett 1993, 522;(h) Chenede, A.;Perri, E.;Rekai, E. D.;
Sinay, P. Synlett 1994, 420;(i) Mallet, J. M.;Sinay , P.
, P.
¨
Lowe, J. B.;Ward, P. A.
Pasquarello, C.;Demange, R.;Vogel, P.
Chem. Lett. 1999, 9, 793;(m) Pasquarello, C.;Picasso, S.;
Nature 1993, 364, 149;
¨
¨
Bioorg. Med.
Tetrahedron: Asymmetry 1994, 5, 2593;(j) Dietrich, H.;
Regele-Mayer, C.;Schmidt, R. R. Carbohydr. Lett. 1994,
Demange, R.;Malissard, M.;Berger, E. G.;Vogel, P.
Org. Chem. 2000, 65, 4251;(n) Rademacher, T. W.;
Parekh, R. B.;Dwek, R. A. Annu. Rev. Biochem. 1988, 57,
785;Lis, H.;Sharon, N. Eur. J. Biochem. 1993, 218, 1;
Hart, G. W. Curr. Opin. Cell. Biol. 1992, 4, 1017;Varki,
A.;Freeze, H. H. In Subcellar Biochemistry;Maddy, A.
H., Harris, J. R., Eds.;Plenum: New York, 1994;pp 71;
Sears, P.;Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38,
2301;Bertozzi, C. R.;Kiesling, L. L. Science (Washington,
DC) 2001, 291, 2357;Rudd, P. M.;Elliott, T.;Cresswell,
P.;Wilson, I. A.;Dwek, R. A. Science (Washington, DC)
2001, 291, 2370.
J.
1, 115;(k) Rubinstenn, G.;Mallet, J.-M.;Sinay
Tetrahedron Lett. 1998, 39, 3697;(l) Helmboldt, A.;
Mallet, J.-M.;Petitou, M.;Sinay , P. Bull. Soc. Chim. Fr.
¨
1997, 134, 1057;(m) Lui, L.;Postema, M. H. D. J. Am.
, P.
¨
Chem. Soc. 2001, 123, 8602;(n) Vauzeilles, B.;Sinay , P.
¨
Tetrahedron Lett. 2001, 42, 7269;(o) Mikkelsen, L. M.;
Skrydstrup, T. J. Org. Chem. 2003, 68, 2123;(p) Postema,
H. M. D.;Piper, J. L.;Liu, L.;Shen, J.;Faust, M.;
Andreada, P. J. Org. Chem. 2003, 68, 4748;(q) Denton, R.
W.;Mootoo, D. R. J. Carbohydr. Chem. 2003, 22, 671.
6. First synthesis of a C-linked disaccharide (b-D-Glcp-
C(1!6)-a-D-Glcp-OMe), see: Rouzaud, D.;Sinay , P. J.
¨
2. Levy, D. E.;Tang, C. In The Chemistry of C-Glycosides,
Tetrahedron Organic Chemistry Series;Baldwin, J. E.,
Magnus, P. D., Eds.;Pergamon–Elsevier Science: Oxford,
1995;Postma, M. H. D. C-Glycoside Synthesis;CRC:
Boca Raton, FL, 1995;Vogel, P.;Ferritto, R.;Kra-
ehenbuehl, K.;Baudat, A. In Carbohydrate Mimics,
Concept and Methods;Vogel Chapleur, Y., Ed.;Wiley–
VCH: Weinheim, 1998;pp 19, and references cited therein;
Du, Y.;Linhardt, R. J.;Vlahov, I. R. Tetrahedron 1998,
54, 9913.
Chem. Soc., Chem. Commun. 1983, 1353.
7. (a) Itoh, A.;Ozawa, S.;Oshima, K.;Nozaki, H.
Tetra-
hedron Lett. 1980, 21, 361;(b) Itoh, A.;Ozawa, S.;
Oshima, K.;Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54,
274.
8. (a) Zhu, Y.-H.;Vogel, P. Tetrahedron Lett. 1998, 39, 31;
(b) Zhu, Y.-H.;Demange, R.;Vogel, P.
Tetrahedron:
´
Asymmetry 2000, 11, 263;(c) Jime nez-Barbero, J.;
Demange, R.;Schenk, K.;Vogel, P. J. Org. Chem. 2001,
66, 5132;(d) Demange, R.;Buhlmann, C.;Vogel, P. Helv.
Chim. Acta 2003, 86, 361.
3. Springer, G. F. Science 1984, 224, 1198;Jennings, H. J.;
Ashton, F. E.;Gamian, A.;Michon, F.;Roy, R.
Can.
9. Zhu, Y.-H.;Vogel, P. J. Org. Chem. 1999, 64, 666.
10. Zhu, Y.-H.;Vogel, P. Chem. Commun. 1999, 1873.
11. Navarro, I.;Vogel, P. Helv. Chim. Acta 2002, 85, 152.
12. Witczak, Z. J.;Chhabra, R.;Chojiracki, J. Tetrahedron
Lett. 1997, 38, 2215.
13. Jeanneret, V.;Meerpoel, L.;Vogel, P. Tetrahedron Lett.
1997, 38, 543.
14. (a) Lowary, T.;Meldal, M.;Helmboldt, A.;Vasella, A.;
Bock, K. J. Org Chem. 1998, 63, 9657;(b) Brenna, E.;
Prog. Biotechnol. 1987, 3, 149;Taylor-Papadimitriou, J.;
Epenetos, A. A. Trends Biotechnol. 1994, 12, 227;
MacLean, G. D.;Reddish, M. A.;Bowen-Yacyshyn, M.
B.;Poppema, S.;Longenecker, B. M. Cancer Invest. 1994,
12, 46;see, for example: Rye, P. D.;Bovin, N. V.;
Vlasova, E. V.;Walker, R. A. Glycobiology 1995, 5, 385;
Springer, G. F. Crit. Rev. Oncog. 1995, 6, 57;Ragupathi,
G. Cancer Immunol. Immunother. 1996, 43, 152;Cooper,
D. K. C.;Oriol, R. Glycobiology. In Xenotransplantation
Research in Glycosciences;Gabius, S., Ed.;Chapman &
Hall: Weinheim, 1997;pp 531;Kim, Y. J.;Varki, A.
Glycoconjugate J. 1997, 14, 569;Hakomori, S.;Zhang, Y.
Chem. Biol. 1997, 4, 97;Hallberg, E. C.;Strokan, V.;
Cairns, T. D. H.;Breimer, M. E.;Samuelsson, B. E.
Xenotransplantation 1998, 5, 246;Hakomori, S. Acta Anat.
1998, 161, 79;Kuduk, S. D.;Schwarz, J. B.;Chen, X.-T.;
Glunz, P. W.;Sames, D.;Ragupathi, G.;Livingston, P.
O.;Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 12474;
Orntoft, T. F.;Vestergaard, E. M. Electrophoresis 1999,
Fuganti, C.;Grasseli, P.;Serra, S.;Zambotti, S.
Chem.
Eur. J. 2002, 8, 1872;(c) Xu, X.;Fakha, G.;Sinou, D.
Tetrahedron 2003, 58, 7539.
15. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1985, 25, 508.
16. (a) Farina, V.;Kapadia, S.;Krisnan, B.;Wang, C.;
Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905;(b) Falck,
J. R.;Bhatt, R. K.;Ye, J. J. Am. Chem. Soc. 1995, 117,
5973.
17. Keinan, E.;Perez, D. J. Org. Chem. 1987, 52, 2576.
18. Rychnovsky, S. D.;Rogers, B. N.;Richardson, T. I. Acc.
Chem. Res. 1998, 31, 9.