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Original Articles

Synthesis of Lewis a and Lewis X Pentasaccharides Based on N-Trichloroethoxycarbonyl ProtectionFootnote1

, &
Pages 739-758 | Accepted 02 Mar 1998, Published online: 22 Aug 2006

References

  • Dedicated to the memory of Professor Akira Hasegawa
  • Schmidt , R. R. and Kinzy , W. 1994 . Adv. Carbohydr. Chem. Biochem. , 50 : 21 H.G. Garg, K. von dem Bruch and H. Kunz, ibid., 50, 227 (1994); and references therein.
  • Lemieux , R. U. , Takeda , T. and Chung , B. Y. 1976 . ACS Symp. Ser. , 39 : 90 J. Banoub, P. Boullanger, and D. Lafont, Chem. Rev., 92, 1167 (1997); D. Lafont and P. Boullanger, J. Curbohydr. Chem., 11, 567 (1992); and references therein.
  • Debenham , J. S. , Madsen , R. , Roberts , C. and Fraser-Reid , B. 1995 . J. Am. Chem. Soc. , 117 : 3302
  • Castro-Palomino , J. C. and Schmidt , R. R. 1995 . Tetrahedron Lett. , 36 : 5343
  • Castro-Palomino , J. C. and Schmidt , R. R. 1995 . Tetrahedron Lett. , 36 : 6871
  • Meinjohanns , E. , Meldal , M. , Paulsen , H. and Bock , K. 1995 . J. Chem. Soc., Perkin Trans. 1 , : 405 K.J. Jensen, P.R. Hansen, D. Venugopal, and G. Barany, J. Am. Chem. SOC., 118, 3148 (1996).
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  • Toepfer , A. , Kinzy , W. and Schmidt , R. R. 1994 . Liebigs Ann. Chem. , : 449 A. Toepfer and R.R. Schmidt, Tetrahedron Lett., 33, 5161 (1992); and references therein.
  • Spijker , N. M. , Westerduin , P. and van Boeckel , C. A. A. 1992 . Tetrahedron , : 6297 Y. Matsuzaki, Y. Ito, Y. Nakahara, and T. Ogawa, Tetrahedron Lett., 34, 1061 (1993); F.A.W. Kolman, J.W.G. Meisener, H.R.P. van Ritter, J.P. Kamerling, and J.F.G. Vliegenthart, J. Carbohydr. Chem., 13, 1 (1994)
  • Debenham , J. , Rodebaugh and Fraser-Reid , B. 1997 . Liebigs Ann. Chem. , : 791
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  • Paulsen , H. and Helpap , B. 1991 . Carbohydr. Res. , 216 : 289
  • Windholz , T. B. and Johnson , D. B. R. 1967 . Tetrahedron Lett. , : 2555 Instead of Teoc the abbreviation Troc has been used in the first paper. For the first use of N-Teoc in a glycosyl donor: S. Kusumoto, H. Yoshimura, M. Imoto, T. Shimamoto, and T. Shiba, Tetrahedron Lett., 26, 909 (1985). For other applications, see: M. Imoto, H. Yoshimura, T. Shimamoto, N. Sakaguchi, S. Kusumoto, and T. Shiba, Bull. Chem. Soc. Jpn., 60, 2205 (1987; P. Boullanger, M. Jouineau, B. Bonammali, D. Lafont, and G. Descotes, Carbohydr. Res., 202, 151 (1990); T. Mukaiyama and K. Matsubara, Chemistry Lett., 1755 (1992); M. Schultz and H. Kunz, Tetrahedron:Asymmetry, 4, 1205 (1993); Tetrahedron Lett. 33, 5319 (1992); V. Pozsgay, Glycoconjugate J., 10, 133 (1993); T. Ziegler, Carbohydr. Res., 262, 195 (1994)
  • Toepfer , A. and Schmidt , R. R. 1993 . J. Carbohydr. Chem. , 12 : 809 For previous syntheses of the Lea and Lex epitopes: ref. 8; R. Windmüller and R.R. Schmidt, Tetrahedron Lett., 35, 7927 (1994); J. Natunen, R. Niemela, L. Penttila, A. Seppo, T. Ruohtula, O. Renkonen, Glycobiology, 4, 577 (1994); G. Hummel and R.R. Schmidt, Tetrahedron Lett., 38, 1173 (1997); and references therein
  • Schmidt , R. R. and Stumpp , M. 1983 . Liebigs Ann. Chem. , : 1249 P.H. Amvam-Zollo and P. Sinaÿ, Carbohydr. Res., 150, 199 (1986); S. Sato, Y. Ito, T. Nukuda, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 167, 197 (1987)
  • Windmüller , R. 1995 . Dissertation Univ. Konstanz .
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  • Schmidt , R. R. and Toepfer , A. 1991 . Tetrahedron Lett. , 32 : 3351
  • Greilich , U. , Brescello , R. , Jung , K.-H. and Schmidt , R. R. 1996 . Liebigs Ann. Chem. , : 663
  • Spijker , N. M. , Keuning , C. A. , Hooglugt , M. , Veeneman , G. H. and van Boeckel , C. A. A. 1996 . Tetrahedron , 52 : 5945
  • Zemplén , G. 1927 . Ber. Dtsch. Chem. Ges. , 60 : 1555

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