Automated chemical synthesis: From resins to instruments

Molecular Diversity

Volumn 2, Issue 4, 1997, Pages 197-206

  Porco Jr , John A ^a   Deegan, Tracy ^a   Devonport, Wayne ^a   Gooding, Owen W ^a   Heisler, Kevin ^a   Labadie, Jeff W ^a   Newcomb, Bill ^a   Nguyen, Cindy ^a   Van Eikeren, Paul ^a   Wong, Jonathan ^a   Wright, Peter ^a  

^a Argonaut Technologies   (United States)

Author keywords

Automated organic synthesis; Chemical synthesis development; Combinatorial chemistry; Linkers; Polymer supports; Solid phase synthesis

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MACROGOL DERIVATIVE; PLANT RESIN; POLYETHYLENE GLYCOL POLYSTYRENE; POLYETHYLENE GLYCOL-POLYSTYRENE; POLYSTYRENE DERIVATIVE;

ARTICLE; AUTOMATION; BIOCHEMISTRY; INSTRUMENTATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TIME;

AUTOMATION; BIOCHEMISTRY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; POLYETHYLENE GLYCOLS; POLYSTYRENES; RESINS, PLANT; TIME FACTORS;

EID: 0031110084     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01715635     Document Type: Article

References (19)

1. Gooding, O., Hoeprich Jr., P.D., Labadie, J.W., Porco Jr., J.A., Van Eikeren, P. and Wright, P., Boosting the productivity of medicinal chemistry through automation tools: Novel technological developments enable a wide range of automated synthetic procedures, In Chaiken, I.M. and Janda, K.D. (Eds.) Molecular Diversity and Combinatorial Chemistry: Libraries and Drug Discovery, American Chemical Society, Washington, DC, U.S.A., pp. 199-206.
2. Fruchtel, J.S. and Jung, G., Organic chemistry on solid supports, Angew. Cheni. Int. Ed. Engl., 35 (1996) 17-42.
3. Labadie, J.W., Deegan, T.L., Gooding, O.W., Heisler, K., Newcomb, W.S., Porco Jr., J.A., Tran, T.H. and Van Eikeren, P., New poly(styrene-oxyethylene) graft copolymers as supports for solidphase organic synthesis, Proc. Am. Chem. Soc. Div. Polym. Mater.: Sci. Eng., 75 (1996) 389-390.
4. Bayer, E. and Rapp, W., Polystyrene-immobilized PEG chains: Dynamics and application in peptide synthesis, immunology, and Chromatograph); In Harris, J.M. (Ed.) Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomédical Applications, Plenum, New York, NY, U.S.A., 1992, pp. 325-345.
5. 13C-NMR to monitor solid phase peptide synthesis, Tetrahedron, 40 (19S4) 4141-4152.
6. 13C-Iabeled compounds to facilitate reaction monitoring, see: Look, G.C., Holmes, C.P., Chinn, J.P. and Gallop, M.A., Methods for combinatorial organic synthesis: The use of fast "C NMR analysis for gel phase reaction monitoring, 3. Org. Chem., 59 (1994) 7588-7590.
7. 2N2 activation of polymer-linked acyl sulfonamides, see: Kenner, G.W., McDermott, J.R. and Sheppard, R.C., The safety catch principle in solid phase peptide synthesis, J. Chem. Soc., Chem. Commun., (1971) 636-637.
8. 2N2, see: Aoyama, T., Terasawa, S., Sudo, K. and Shioiri, T., A'cii- methods and reagents in organic synthesis. Trimethylsilyldiazomethane: A convenient reagent for the O-meihylation of phenols and enols, Chem. Pharm. Bull.; 32 (1984) 3759-3760.
9. 2 resin'.
10. For a recent review, see: Hughes, D.L., The Mitsimobit reaction, Org. Reactions, 42 (1992) 337-636.
11. Rano, T.A. and Chapman, K.T., Solid-phase synthesis ofaryl ethers ïa the Mitsimobu reaction, Tetrahedron Lett., 36 (1995) 3789-3792.
12. Krchnâk, V., Flegelova, Z., Weichsel, A.S. and Lebl, M., Polymer-supported Mitsunobu ether formation and its use in combinatorial chemistry, Tetrahedron Lett., 36 (1995) 6193-6196.
13. For isoxazole formation using esters, see: He, Y. and Lin, N.-H., Studies on isoxazole formation from alkyl carboxylic esters. Synthesis, (1994) 989-992.
14. For isoxazole formation employing Weinreb amides, see: Nitz, T.J., Volkots, D.L., Aldous, D.J. and Oglesby, R.C., Regiospecific synthesis of 3-siibstituted5-alkyliso azolesfroni oxime dianions and N-methoxy-N-methylalkylamides, 3. Org. Chem., 59 (1994) 5828-5832.
15. For the synthesis of C-terminal peptide aldehydes by reactions of LiAlHj with Weinreb-type amides on solid support, see: Fehrentz, J.-A., Paris, M., Heitz, A., Velek, J., Liu, C.-F, Winternitz, F. and Martinez, J., Improved solid phase synthesis of C-terminal peptide aldehydes, Tetrahedron Lett., 36 (1995) 7871-7874.
16. Dinh, T.Q. and Armstrong, R.W., Synthesis ofketones and aldehydes via reactions of Weinreb-type amides on solid support, Tetrahedron Lett., 37 (1996) 1161-1164.
17. Cf. Dressman, B.A., Spangle, L.A. and Kaldor, S.W., Solid phase synthesis ofhydanloins using a carbamale linker and a novel cyclizationlcleavage step, Tetrahedron Lett., 37 (1996) 937-940.
18. For a recent review on the Suzuki cross-coupling, see: Miyaura, N. and Suzuki, A., Palladium-catalyzed cross-coupling reactions of organoboron compounds, Chem. Rev., 95 (1995) 2457-2483.
19. Backes, B.J. and Ellman, J.A., Carbon-carbon bond-forming methods on solid support. Utilization of Kenner's 'safety-catch' linker, J. Am. Chem. Soc., 116 (1994) 11171-11172.