Development of new dihydropyran linker for solid-phase reaction

Archives of Pharmacal Research

Volumn 22, Issue 6, 1999, Pages 585-591

  Ryu, Joon Hyung ^a   Jeong, Jin Hyun ^a  

^a Kyung Hee University   (South Korea)

Author keywords

Carbohydrate library; Combinatorial chemistry; DDHP resin; Dihydropyran linker; Solid phase reaction; Wang resin

Indexed keywords

ALCOHOL DERIVATIVE; CARBOHYDRATE; PLANT RESIN; PYRAN DERIVATIVE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CONFORMATION; DRUG SCREENING; METHODOLOGY; SYNTHESIS;

ALCOHOLS; CARBOHYDRATE CONFORMATION; CARBOHYDRATES; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG EVALUATION; PYRANS; RESINS, PLANT;

EID: 0033255902     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02975331     Document Type: Article

References (32)

1. Armstrong, R. W., Combs, A., Tempest, P. A., Brown, S. D. and Keating, T. A., Multiple-component condensation strategies for combinatorial library synthesis., Acc. Chem. Res., 123 (1996).
2. Balkenhohl, F., Hunnefeld, C.B., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules. Angew. Chem. Int. Ed. Engl., 35, 2288 (1996).
3. Basha, A., Lipton, M. and Weinreb, S. M., A mild, general method for conversion of esters to amindes., Tetrahedron Lett., 4171 (1977).
4. Bernady, K. F., Floyd, M. B., Polettom J. F. and Weiss, M. J., Prostaglandins and Congeners.20. Synthesis of Prostaglandins via Conjugate Addition of Lithium trans-1-Alkenyltrialkylalanate Reagents. A Novel Reagent for Conjugate 1,4-Additions, J. Org. Chem., 44, 1438 (1979).
5. Bunin, B. A. and Ellman, J. A., A general and expedient method for the solid-phase synthesis of 1,4-benzoliazepine derivatives. J. Am. Chem. Soc., 114, 10997 (1992).
6. Bunnin, B. A., Plunkett, M. J. and Ellman, J. A., The combinational synthesis and chemical and biological evaluation of a 1,4-benzodiazepine library. Proc. Natl. Acad. Sci. USA, 4708 (1994).
7. Corey, E. J., Enders, D., Synthesewege zu polyfunktionellen Molekülen über metallerte Dimethylhydrazone, Chem. Ber., 111, 1362 (1978).
8. Corey, E. J., Niwa, H. and Knolle, J., Total synthesis of (S)-12- hydroxy -5,8,14- cis- 10-trans - eicosatetraenoic acid (Samuelsson's HETE). J. Am. Chem. Soc., 100, 1942 (1978).
9. Corey, E. J. and Venkateswarlu, A., Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J. Am. Chem. Soc., 94, 6190 (1972).
10. Dewitt, S. H. and Czarnik, A. W., Combinatorial organic synthesis using parke-davis's DIVERSOMER method., Acc. Chem. Res., 114 (1996).
11. Frechet, J. M. J., in Polymer-supported Reactions in Organic Synthesis, Hodge, P., and Sherrington, D.C.(Eds.), Wiley, 294 (1980).
12. Dolle, R. E. and Nelson, Jr., K. H., Comprehensive survey of combinatorial library synthesis: 1998. J. Combi. Chem., 1, 235 (1999).
13. Ellman, J. A., Design, synthesis, and evaluation of small-molecule., Acc. Chem. Res., 132 (1996).
14. Gordon, E. M., Gallop, M. A. and Patel, D. V., Strategy and tactics in combinatorial organic synthesis. Applications to drung discovery. Acc. Chem. Res., 144 (1996).
15. Kendall, P. M., Johnson, J. V., and Cook, C. E., Synthetic Route to an Aromatic Analogue of Strigol, J. Org. Chem., 44, 1421 (1979).
16. Kobayashi, S., New methodologies for the synthesis of compound libraries. Chem. Soc. Rev., 28, 1 (1999).
17. Kociensky, C.m Yeates, C., A New synthesis of 1,7-dioxaspiro[5,5]undecanes. Application to a rectal gland secretion of the olive fly (Dacus oleae), Tetrahedron Lett., 3905 (1983).
18. Levin, J. I., Turos, E. and Weinreb, S. M., An alternative procedure for the aluminum-mediated conversion of esters to amides. Synthetic Comm., 989 (1992).
19. Liu, G. and Ellman, J. A., Straighforward and general method for coupling alcohols to solid supports, Tetrahedron Lett., 35, 9333 (1994).
20. Liu, G. and Ellman, J. A., A general solid-phase synthesis strategy for the preparation of 2-pyrrolidinemethanol ligands. J. Org. Chem., 60, 7712 (1995).
21. Miyashita, M., Yoshikoshi, A. and Grieco, P. A., Pyridinium p-toluenesulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols. J. Org. Chem., 42, 3772 (1977).
22. Nahm, S. and Weinreb S. M., N-Methoxy-N-methylamides as effective acylating agents., Tetrahedron Lett., 3815 (1981).
23. Nugiel, D., Cornelius, L. A. M., Corbett, J. W., Facile Preparation of 2,6-Disubstituted Purines Using Solid-Phase Chemistry, J. Org. Chem., 62, 201 (1997).
24. Pearson, W. J., Clark, R. B., Solid-phase synthesis of pyrrolidines via 2-azaallyl anion cycloadditions with alkenes, Tetrahedron Lett., 38, 7669 (1997).
25. Petsko, G. A., For medicinal purposes. Nature., 384, 7 (1996).
26. Ronald, R. C., Lansinger, J. M., Lillie, T. S., and Wheeler, C. J., Total synthesis of frustulosin and aurocitrin. J. Org. Chem., 47, 2541(1982).
27. Still, W. C., Kahn, M. and Mitra, A., Rapid chromatographic technique for preparative separations with moderate resolution. J. Org. Chem., 43, 2923 (1978).
28. Thompson, L. A., and Ellman, J. A., Straightforward and general method for coupling alcohols to solid supports. Tetrahedron Lett., 35, 9333 (1994).
29. Thompson, L. A. and Ellman, J. A., Synthesis and applications of small molecule libraries. Chem. Rev., 96, 555 (1996).
30. Wallace, O. B., Solid phase synthesis of ketones from esters, Tetrahedron Lett., 38, 4939 (1997).
31. Wang, S. S., Solid phase synthesis of protected peptides via photolytic cleavage of the α-Methylphenacyl ester anchoring linkage. J. Org. Chem., 41, 3258 (1976).
32. Yoo, S. E., Seo, J. -S.; Yi, K. -Y.; Gong, Y. -D., Solid phase synthesis of biphenyltetrazole derivatives, Tetrahedron Lett., 38, 1203 (1997).