Solid-phase synthesis of oligosaccharides: Construction of a dodecasaccharide

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1559-1561

  Nicolaou, K C ^a   Watanabe, Nobuhide ^a   Li, Jim ^a   Pastor, Joaquín ^a   Winssinger, Nicolas ^a  

^a NONE

Author keywords

Block type construction; Oligosaccharides; Photolabile linker; Solid phase synthesis; Thioglycoside

Indexed keywords

EID: 0032547050     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1559::AID-ANIE1559>3.0.CO;2-E     Document Type: Article

References (33)

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11. For related work prior to August 1996, see ref. [2]. For recent work, see a) R. Rodehaugh, S. Joshi, B. Fraser-Reid, M. H. Geysen, G. M. Paul, J. Org. Chem. 1997, 62, 5660-5661; b) J. Rademann, R. R. Schmidt, ibid. 1997, 62, 3650-3653; c) I. Yukishige, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562-5566; d) R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, C. W. Still, D. Kahne, Science 1996, 274, 1520-1522; e) Y. Ito, O. Kanie, T. Ogawa, Angew. Chem. 1996, 108, 2691-2693; Angew. Chem. Int. Ed. Engl. 1996, 35, 2510-2512.
12. For related work prior to August 1996, see ref. [2]. For recent work, see a) R. Rodehaugh, S. Joshi, B. Fraser-Reid, M. H. Geysen, G. M. Paul, J. Org. Chem. 1997, 62, 5660-5661; b) J. Rademann, R. R. Schmidt, ibid. 1997, 62, 3650-3653; c) I. Yukishige, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562-5566; d) R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, C. W. Still, D. Kahne, Science 1996, 274, 1520-1522; e) Y. Ito, O. Kanie, T. Ogawa, Angew. Chem. 1996, 108, 2691-2693; Angew. Chem. Int. Ed. Engl. 1996, 35, 2510-2512.
13. For related work prior to August 1996, see ref. [2]. For recent work, see a) R. Rodehaugh, S. Joshi, B. Fraser-Reid, M. H. Geysen, G. M. Paul, J. Org. Chem. 1997, 62, 5660-5661; b) J. Rademann, R. R. Schmidt, ibid. 1997, 62, 3650-3653; c) I. Yukishige, T. Ogawa, J. Am. Chem. Soc. 1997, 119, 5562-5566; d) R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, C. W. Still, D. Kahne, Science 1996, 274, 1520-1522; e) Y. Ito, O. Kanie, T. Ogawa, Angew. Chem. 1996, 108, 2691-2693; Angew. Chem. Int. Ed. Engl. 1996, 35, 2510-2512.
14. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
15. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
16. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
17. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
18. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
19. For a number of previous photolabile linkers used for solid-phase oligosaccharide synthesis, see a) U. Zehavi, B. Amit, A. Patchornik, J. Org. Chem. 1972, 14, 2281-2285; b) ref. [3a] ; for previous syntheses of photolabile linkers, see c) C. P. Holmes, D. G. Jones, J. Org. Chem. 1995, 8, 2318-2321; d) H. Venkatesan, M. M. Greenberg, ibid. 1996, 61, 525-529; e) A. Ajayagosh, R. V. N. Pillai, Tetrahedron Lett. 1995, 36, 777-780; for a review of photolabile protecting groups, see R. V. N. Pillai in Organic Photochemistry, Vol. 9 (Ed.: A. Padwa), Marcel Dekker, New York, 1987, p. 225.
20. Yield based on polymer mass gain.
21. The β-stereochemistry of this and subsequent glycosidations was ensured by the benzoate group at the C-2 position of the glycosyl donors. Thioglycosides A-C were prepared by standard methods; details will be reported in the full account of this work.
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24. The yield for this and subsequent steps were based on isolated material obtained by photolytic cleavage. Yields refer to spectroscopically and chromatographically homogeneous materials.
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26. Compound A′ was obtained as a mixture of α and β anomers (ca. 1:1).
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31. Polymer conjugates 10, 11, and 13 were analyzed directly by on-bead Matrix Assisted Laser Desorption Ionization (MALDI) mass spectroscopy; see a) G. Siuzdak, J. K. Lewis, Combinatorial Chemistry, in press; b) M. C. Fitzgerald, K. Harris, C. G. Shelvin, G. Siuzdak, Bioorg. Med. Chem. Lett. 1996, 6, 979-982.
32. A-3 proton signals increased by one respectively.
33. Yields refer to isolated, spectroscopically homogenous materials.