Synthesis of glucopyranosyl amides using polymer-supported reagents

Synthetic Communications

Volumn 34, Issue 13, 2004, Pages 2499-2506

  Root, Yuriko Y ^a   Bailor, Maximillian S ^b   Norris, Peter ^a  

^a YOUNGSTOWN STATE UNIVERSITY   (United States)

^b GRINNELL COLLEGE   (United States)

Author keywords

Glycosyl amides; Polymer bound iminophosphorane; Polymer supported reagents; Triphenylphosphine

Indexed keywords

AMIDE; AZIDE; GLUCOSE DERIVATIVE; POLYMER; REAGENT; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 3543068270     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120039504     Document Type: Article

References (13)

1. Davis, B.G. Synthesis of glycoproteins. Chem. Rev. 2002, 102, 579-601.
2. Rottmann, A.; Synstad, B.; Eijsink, V.; Peter, M.G. Synthesis of N-acetylglucos-aminyl and diacetylchitobiosyl amides of heterocyclic carboxylic acids as potential chitinase inhibitors. Eur. J. Org. Chem. 1999, 2293-2297.
3. Boullanger, P.; Maunier, V.; Lafont, D. Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosyl-amines. Carbohydr. Res. 2000, 324, 97-106.
4. Pleuss, N.; Kunz, H. N-Glycosyl amides: removal of the anomeric protecting group and conversion into glycosyl donors. Angew. Chem. int. Ed. 2003, 42, 3174-3176.
5. Murphy, P.V.; Pitt, N.; O'Brien, A.; Enright, P.M.; Dunne, A.; Wilson, S.J.; Duane, R.M.; O'Boyle, K.M. Identification of novel inhibitors of fibroblast growth factor (FGF-2) binding to heparin and endothelial cell survival from a structurally diverse carbohybrid library. Bioorg. Med. Chem. Lett. 2002, 12, 3287-3290.
6. Paulsen, H.; Pflughaupt, K.W. Glycosylamines. In The Carbohydrates, Chemistry and Biochemistry; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1980; 881-927.
7. Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Gyorgydeák, Z. An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides. Tetrahedron 2001, 57, 4609-4621.
8. Murphy, P.V.; Bradley, H.; Tosin, M.; Pitt, N.; Fitzpatrick, G.M.; Glass, W.K. Development of carbohydrate-based scaffolds for restricted presentation of recognition groups. Extension to divalent ligands and implications for the structure of dimerized receptors. J. Org. Chem. 2003, 68, 5692-5704.
9. Garcia, J.; Urpi, F.; Vilarrasa, J. New synthetic tricks. Triphenylphosphine-mediated amide formation from carboxylic acids and azides. Tetrahedron Lett. 1984, 25, 4841-4844.
10. Garcia-Moreno, M.I.; Diaz-Pérez, P.; Benito, J.M.; Mellet, C.O.; Defaye, J.; Fernández, J.M.G. One-step synthesis of non-anomeric sugar isothiocyanates from sugar azides. Carbohydr. Res. 2002, 337, 2329-2334.
11. Ibatullin, F.M.; Shabalin, K.A. A simple and convenient synthesis of glycosyl azides. Synth. Commun. 2000, 30, 2819-2823 (and references cited therein).
12. www.argotech.com.
13. Bhalay, G.; Dunstan, A.; Glen, A. Supported reagents: opportunities and limitations. Synlett 2000, 1846-1859.