Solid phase synthesis of oligosaccharides

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 5007-5010

  Adinolfi, Matteo ^a   Barone, Gaspare ^a   De Napoli, Lorenzo ^a   Iadonisi, Alfonso ^a   Piccialli, Gennaro ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE GLYCOL; OLIGOSACCHARIDE; POLYSTYRENE;

AMINO ACID ANALYSIS; ARTICLE; DRUG SYNTHESIS; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTEIN SYNTHESIS; SPECTROPHOTOMETRY;

EID: 0030575428     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01020-9     Document Type: Article

References (27)

1. 1. a) L. A. Lasky, Science 1992, 258, 964;
2. b) A. Varki, Glycobiology, 1993, 3, 97.
3. 2. Reviews on glycoside synthesis: a) H. Paulsen, Angew. Chem., 1982, 94, 184;
4. b) R. R. Schmidt, Angew. Chem., 1986, 98, 213;
5. c) K. Toshima, K. Tatsuta, Chem. Rev., 1993, 93, 1503;
6. d) C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. Int. Ed Engl., 1995, 34, 412; and 521;
7. e) G.-I. Boons, Tetrahedron, 1996, 4, 1095.
8. 3. For example see: a) S. P. Douglas, D. M. Whitfield, J. J Krepinsky, J. Am. Chem. Soc., 1991, 113, 5095; S.-I. Nishimura, K. Matsouka, Y.C. Lee, Tetrahedron Lett., 1994, 35, 5657.
9. 3. For example see: a) S. P. Douglas, D. M. Whitfield, J. J Krepinsky, J. Am. Chem. Soc., 1991, 113, 5095; S.-I. Nishimura, K. Matsouka, Y.C. Lee, Tetrahedron Lett., 1994, 35, 5657.
10. 4. For example see: a) S. J. Danishefsky, K. F. McClure, J. T. Randolph, R. B. Ruggeri, Science, 1993, 260, 1307;
11. b) M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong , J. Am. Chem. Soc., 1994, 116, 1135;
12. c) L. Yan, C. M. Taylor, R. Godnow, D. Kahne, J. Am. Chem. Soc., 1994, 116, 6953.
13. 5. Commercially available from Rapp Polymer, Tubingen, Germany.
14. 6. E. Bayer, Angew. Chem. Int. Ed. Engl., 1991, 30, 113
15. 7. a) H. Gao, B.L. Gaffney, R.A. Jones, Tetrahedron Lett., 1991, 32, 5477;
16. b) L. De Napoli, A. Galeone, L.Mayol, A. Messere, D. Montesarchio, G. Piccialli, Biorganic & Medicinal Chemistry, 1995, 3, 1325.
17. +.
18. +.
19. +.
20. 11. All the operations on the solid supports were performed in a short glass column equipped with a sintered glass filter, a stopcock and an Aldrich rubber cap.
21. 12. R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed Engl. 1980, 19, 731.
22. 13. T. Iversen, D. R. Bundle, J. Chem. Soc. Chem. Commun., 1981, 1240.
23. 14. A. Toepfer, R. R. Schmidt, J. Carbohydr. Chem., 1993, 12, 809.
24. 15 G. Böhm, H. Waldmann, Tetrahedron Lett., 1995, 36, 3843.
25. 2O), methoxyl signals of 1 at δ 3.45 and of the dimer 13a at δ 3.47.
26. 3), 2.14, 2.10, 2.09, 2.04, 2.03, 2.00, 1.98 (3H each, s's, MeCO)
27. 18. M. Forsgren, P.-E. Jansson, L. Kenne, J. Chem. Soc. Perkin Trans. 1, 1985, 2383.