Synthesis of arrays using low molecular weight MPEG-assisted mitsunobu reaction

ACS Combinatorial Science

Volumn 13, Issue 3, 2011, Pages 280-285

  Figlus, Marek ^a   Wellaway, Natalie ^b   Cooper, Anthony W J ^b   Sollis, Steven L ^b   Hartley, Richard C ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

cLogP; Mitsunobu reaction; solid phase extraction; triphenylphosphine

Indexed keywords

ARTICLE; COMBINATORIAL CHEMISTRY; MOLECULAR WEIGHT; SOLID PHASE EXTRACTION;

COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR WEIGHT; SOLID PHASE EXTRACTION;

EID: 79955822937     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co100091n     Document Type: Article

References (29)

1. Review: Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Mitsunobu and Related Reactions: Advances and Applications Chem. Rev. 2009, 109, 2551-2651
2. Ley, S. V.; Ladlow, M.; Vickerstaffe, E. In Exploiting Chemical Diversity for Drug Discovery; Bartlett, P. A.; Entzeroth, M., Eds.; The Royal Society of Chemistry: Cambridge, U.K., 2006; Chapter 1, pp 3 - 32.
3. Barrett, A. G. M.; Roberts, R. S.; Schröder, J. Impurity Annihilation: Chromatography-Free Parallel Mitsunobu Reactions Org. Lett. 2000, 2, 2999-3001
4. Pelletier, J. C.; Kincaid, S. Mitsunobu Reaction Modifications Allowing Product Isolation without Chromatography: Application to a Small Parallel Library Tetrahedron Lett. 2000, 41, 797-800 (Pubitemid 30089881)
5. Lan, P.; Porco, J. A., Jr.; South, M. S.; Parlow, J. J. The Development of a Chromatography-Free Mitsunobu Reaction: Synthesis and Applications of an Anthracene-Tagged Phosphine Reagent J. Comb. Chem. 2003, 5, 660-669 (Pubitemid 37206172)
6. Egelhaaf, H.-J.; Rademann, J. Understanding Supported Reactions in Spherical Compartments: A General Algorithm To Model and Determine Rate Constants, Diffusion Coefficients, and Spatial Product Distributions J. Comb. Chem. 2005, 7, 929-941 (Pubitemid 41709512)
7. Czarnik, A. W. Solid-Phase Synthesis Supports Are Like Solvents Biotechnol. Bioeng. (Comb. Chem.) 1998, 61, 77-79 (Pubitemid 28561947)
8. Chen, C. H.-T.; Zhang, W. Fluorous Reagents and Scavengers Versus Solid-Supported Reagents and Scavengers, a Reaction Rate and Kinetic Comparison Mol. Diversity 2005, 9, 353-359 (Pubitemid 41719669)
9. Hagiya, K.; Muramoto, N.; Misaki, T.; Sugimura, T. DMEAD: A New Dialkyl Azodicarboxylate for the Mitsunobu Reaction Tetrahedron 2009, 65, 6109-6114
10. Kiankarimi, M.; Lowe, R.; McCarthy, J. R.; Whitten, J. P. Diphenyl 2-Pyridylphosphine and Di-tert-butyl Azodicarboxylate: Convenient Reagents for the Mitsunobu Reaction Tetrahedron Lett. 1999, 40, 4497-4500 (Pubitemid 29251651)
11. Camp, D.; Jenkins, I. D. The Use of a Phosphine Containing a Basic Group in the Mitsunobu Esterification Reaction Aust. J. Chem. 1988, 41, 1835-1839
12. Von Itzstein, M.; Mocerino, M. (p-Dimethylaminophenyl)diphenylphosphine: A More Practical Phosphine in the Mitsunobu Reaction Synth. Commun. 1990, 20, 2049-2057
13. Ginisty, M.; Roy, M.-N.; Charette, A. B. Tetraarylphosphonium-Supported Carbodiimide Reagents: Synthesis, Structure Optimization and Applications J. Org. Chem. 2008, 73, 2542-2547 (Pubitemid 351482961)
14. Sieber, F.; Wentworth, P.; Toker, J. D.; Wentworth, A. D.; Metz, W. A.; Reed, N. N.; Janda, K. D. Development and Application of a Poly(ethyleneglycol)- Supported Triarylphosphine Reagent: Expanding the Sphere of Liquid-Phase Organic Synthesis J. Org. Chem. 1999, 64, 5188-5192
15. Roller, S.; Zhou, H.; Haag, R. High-Loading Polyglycerol Supported Reagents for Mitsunobu- And Acylation-Reactions and Other Useful Polyglycerol Derivatives Mol. Diversity 2005, 9, 305-316 (Pubitemid 41719664)
16. Harned, A. M.; He, H. S.; Toy, P. H.; Flynn, D. L.; Hanson, P. R. Multipolymer Solution-Phase Reactions: Application to the Mitsunobu Reaction J. Am. Chem. Soc. 2005, 127, 52-53 (Pubitemid 40094360)
17. Maity, P. K.; Rolfe, A.; Samarakoon, T. B.; Faisal, S.; Kurtz, R. D.; Long, T. R.; Schätz, A.; Flynn, D. L.; Grass, R. N.; Stark, W. J.; Reiser, O.; Hanson, P. R. Monomer-on-Monomer (MoM) Mitsunobu Reaction: Facile Purification Utilizing Surface-Initiated Sequestration Org. Lett. 2011, 13, 8-10
18. Dandapani, S.; Curran, D. P. Fluorous Mitsunobu Reagents and Reactions Tetrahedron 2002, 58, 3855-3864 (Pubitemid 34465657)
19. Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
20. Review of recent libraries including those using fluorous synthesis and reagents: Dolle, R. E.; Le Bourdonnec, B.; Worm, K.; Morales, G. A.; Thomas, C. J.; Zhang, W. Comprehensive Survey of Chemical Libraries for Drug Discovery and Chemical Biology: 2009 J. Comb. Chem. 2010, 12, 765-806
21. On the basis of the advertised price in dollars of 1 kg of FluoroFlash silica (40 μm particle size) from a specialist supplier of fluorous chemicals and 1 kg of silica (35-70 μm particle size, 60 Å) from a supplier of fine chemicals and chromatographic materials, both accessed online fourth March 2011. Many research institutes and universities already buy silica in bulk at a considerably lower cost.
22. Figlus, M.; Tarruella, A. C.; Messer, A.; Sollis, S. L.; Hartley, R. C. Low Molecular Weight MPEG-assisted Organic Synthesis Chem. Commun. 2010, 46, 4405-4407
23. Low molecular weight MPEG has been used to tag intermediates in the solution-phase synthesis of oligosaccharides: Hanashima, S.; Inamori, K.; Manabe, S.; Taniguchi, N.; Ito, Y. Systematic Synthesis of Bisubstrate-Type Inhibitors of N -Acetylglucosaminyltransferases Chem.? - ?Eur. J. 2006, 12, 3449-3462 and references therein. Jiang, L.; Hartley, R. C.; Chan, T.-H. Use of Low Molecular Weight Polyethylene Glycol Linker for Polymer-Supported Solution Synthesis of Oligosaccharides Chem. Commun. 1996, 2193-2194
24. A heavy MPEG version of this compound has recently been reported and its silver complexes used in NMR studies: Bergbreiter, D. E.; Yang, Y.-C. Variable-Temperature NMR Studies of Soluble Polymer-Supported Phosphine-Silver Complexes J. Org. Chem. 2010, 75, 873-878
25. Leeson, P. D.; Springthorpe, B. The Influence of Drug-like Concepts on Decision-making in Medicinal Chemistry Nature Rev. Drug Discovery 2007, 6, 881-890 (Pubitemid 350042396)
26. ClogP was calculated using Daylight clogP, version 4.81, Daylight Chemical Information Systems, Inc., 28202 Cabot Road, Suite 300, Laguna Niguel, CA 92677.
27. Cooper, T. W. J.; Campbell, I. B.; Macdonald, S. J. F. Factors Determining the Selection of Organic Reactions by Medicinal Chemists and the Use of These Reactions in Arrays (Small Focused Libraries) Angew. Chem., Int. Ed. 2010, 49, 8082-8091
28. Review: Böhm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Müller, K.; Obst-Sander, U.; Stahl, M. Fluorine in Medicinal Chemistry ChemBioChem. 2004, 5, 637-643 (Pubitemid 39257085)
29. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.; Wiley: New York, 2002.