Synthesis of two D-glucosamine derived 3,4-epoxides as potential scaffolds for combinatorial chemistry

Journal of Carbohydrate Chemistry

Volumn 22, Issue 3-4, 2003, Pages 179-184

  Svejgaard, Lars ^a,d   Fuglsang, Henrik ^a,e   Jensen, Peter B ^a   Kelly, Nicholas M ^a,f   Pedersen, Henrik ^b   Andersen, Kim ^b   Ruhland, Thomas ^b   Jensen, Knud J ^c,g  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b H LUNDBECK A S   (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

^d NOVO NORDISK A S   (Denmark)

^e Arpida Ltd   (Switzerland)

^f ACADIA PHARMACEUTICALS INC   (United States)

^g KVL   (Denmark)

Author keywords

3,4 epoxide; Amino; D Glucosamine; Opening; Regioselective O tosylation

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; GLUCOSAMINE DERIVATIVE;

ALLYLATION; AMINATION; ARTICLE; COMBINATORIAL CHEMISTRY; CONFORMATIONAL TRANSITION; DRUG SYNTHESIS; GLYCOSYLATION; QUANTUM YIELD; RIGIDITY; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 0038142846     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120021699     Document Type: Article

References (18)

1. Terret, N.K. Combinatorial Chemistry; Oxford University Press: Oxford, 1998.
2. Bunin, B.A. The Combinatorial Index; Academic Press: San Diego, 1998.
3. Hirschmann, R.; Nicolaou, K.C.; Pietranico, S.; Salvino, J.; Leahy, E.M.; Sprengeler, P.A.; Furst, G.; Smith, A.B.; Strader, C.D.; Cascieri, M.A.; Candelore, M.R.; Donaldson, C.; Vale, W.; Maechler, L. Nonpeptidal peptidomimetics with a β-D-glucose scaffolding. A partial somatostatin agonist bearing a close structural relationship to a potent, selective substance P antagonist. J. Am. Chem. Soc. 1992, 114, 9217-9218.
4. Hirschmann, R.; Nicolaou, K.C.; Pietranico, S.; Leahy, E.M.; Salvino, J.; Arison, B.; Cichy, M.A.; Spoors, P.G.; Shakespeare, W.C.; Sprengeler, P.A.; Hamley, P.; Smith, A.B.; Reisine, T.; Raynor, K.; Maechler, L.; Donaldson, C.; Vale, W.; Freidinger, R.M.; Cascieri, M.R.; Strader, C.D. The versatile steroid nucleus: design and synthesis of a peptidomimetic employing this novel scaffold. J. Am. Chem. Soc. 1993, 115, 12550-12568.
5. Sofia, M.J.; Hunter, R.; Chan, T.Y.; Vaughan, A.; Dulina, R.; Wang, H.; Gange, D. Carbohydrate-based small-molecule scaffolds for the construction of universal pharmacophore mapping libraries. J. Org. Chem. 1998, 63, 2802-2803.
6. Silva, D.J.; Sofia, M.J. Novel carbohydrate scaffolds. Assembly of a uridine-mannose scaffold based on tunicamycin. Tetrahedron Lett. 2000, 41, 855-858.
7. Kallus, C.; Opatz, T.; Wunberg, T.; Schmidt, W.; Henke, S.; Kunz, H. Combinatorial solid-phase synthesis using D-galactose as a chiral five-dimensional diversity scaffold. Tetrahedron Lett. 1999, 40, 7783-7786.
8. Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Carbohydrates as multifunctional chiral scaffolds in combinatorial synthesis. Angew. Chem. Int. Ed. 1998, 37, 2503-2505.
9. Brill, W.K.-D.; De Mesmaeker, A.; Wendeborn, S. Solid-phase synthesis of levoglucosan derivatives. Synlett 1998, 1085-1090.
10. Hirschmann, R.; Decry, L.; Smith, A.B. Development of an efficient, regio- and stereoselective route to libraries based on the β-D-glucose scaffold. J. Org. Chem. 2000, 65, 8307-8316.
11. Sofia, M.J.; Silva, D.J. Recent developments in solid- and solution-phase methods for generating carbohydrate libraries. Curr. Opin. Drug Discov. Dev. 1999, 2, 365-376.
12. Tolborg, J.F.; Jensen, K.J. Solid-phase oligosaccharide synthesis with tris(alkoxy)benzyl amine (BAL) safety-catch anchoring. Chem. Commun. 2000, 147-148.
13. Petersen, L.; Jensen, K.J. DISAL glycosyl donors for efficient glycosylations under acidic conditions: application to solid-phase oligosaccharide synthesis. J. Chem. Soc., Perkin Trans. 1 2001, 2175-2182.
14. Suami, T.; Tadano, K.; Iimura, Y.; Tanabe, H. Direct conversion of D-glucosamine into D-gulosamine. Carbohydr. Res. 1985, 135, 319-323.
15. Jiao, H.; Hindsgaul, O. The 2-N,N-dibenzylamino group as a participating group in the synthesis of β-glycosides. Angew. Chem. Int. Ed. 1999, 38, 346-348.
16. Jensen, K.J.; Alsina, F.; Songster, M.F.; Vagner, J.; Albericio, F.; Barany, G. Backbone amide linker (BAL) strategy for solid-phase synthesis of C-terminal-modified and cyclic peptides. J. Am. Chem. Soc. 1997, 120, 5441-5452.
17. Ellervik, U.; Magnusson, G. A high yielding chemical synthesis of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide; examples of regio- and stereodifferentiated glycosylations. J. Org. Chem. 1998, 63, 9314-9322.
18. x oligosaccharide on polymeric support. J. Am. Chem. Soc. 2000, 122, 10222-10223.