메뉴 건너뛰기




Volumn 5, Issue 5, 2003, Pages 660-669

The development of a chromatography-free mitsunobu reaction: Synthesis and applications of an anthracene-tagged phosphine reagent

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ANTHRACENE; DICARBOXYLIC ACID DERIVATIVE; MALEIMIDE; PHOSPHINE; POLYMER; REAGENT; RESIN;

EID: 0141572268     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc030028h     Document Type: Article
Times cited : (42)

References (48)
  • 1
    • 0036653673 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (2002) Curr. Opin. Drug Discovery Dev. , vol.5 , pp. 580-593
    • Flynn, D.L.1    Berk, S.C.2    Makara, G.M.3
  • 2
    • 0036691029 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (2002) Na. Rev. Drug Discovery , vol.1 , pp. 573-586
    • Ley, S.V.1    Baxendale, I.R.2
  • 3
    • 20844433475 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 3815-4195
    • Ley, S.V.1    Baxendale, I.R.2    Bream, R.N.3    Jackson, P.S.4    Leach, A.G.5    Longbottom, D.A.6    Nesi, M.7    Scott, J.S.8    Storer, R.I.9    Taylor, S.J.10
  • 4
    • 0033152131 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 320-336
    • Parlow, J.J.1    Devraj, R.V.2    South, M.S.3
  • 5
    • 0032948663 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 18-26
    • Booth, R.J.1    Hodges, J.C.2
  • 6
    • 0002369226 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (1998) J. Curr. Opin. Drug Discovery Dev. , vol.1 , pp. 41-50
    • Flynn, D.L.1    Devraj, R.V.2    Parlow, J.3
  • 7
    • 0031152048 scopus 로고    scopus 로고
    • For review, see: (a) Flynn, D. L.; Berk, S. C.; Makara, G. M. Curr. Opin. Drug Discovery Dev. 2002, 5, 580-593. (b) Ley, S. V.; Baxendale, I. R. Na. Rev. Drug Discovery 2002, 1, 573-586. (c) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. (d) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336. (e) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26. (f) Flynn, D. L.; Devraj, R. V.; Parlow, J. J. Curr. Opin. Drug Discovery Dev. 1998, 1, 41-50. (g) Kaldor, S. W.; Siegel, M. G. Curr. Opin. Chem. Biol. 1997, 1, 101-106.
    • (1997) Curr. Opin. Chem. Biol. , vol.1 , pp. 101-106
    • Kaldor, S.W.1    Siegel, M.G.2
  • 10
    • 85077634689 scopus 로고
    • For review, see: (a) Mitsunobu, O. Synthesis 1981, 1-28. (b) Simon, C.; Sandor, H.; Sandor, M. J. Heterocycl. Chem. 1997, 34, 349. (c) Hughes, D. L. Org. Reactions 1992, 42, 335.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 11
    • 0030941221 scopus 로고    scopus 로고
    • For review, see: (a) Mitsunobu, O. Synthesis 1981, 1-28. (b) Simon, C.; Sandor, H.; Sandor, M. J. Heterocycl. Chem. 1997, 34, 349. (c) Hughes, D. L. Org. Reactions 1992, 42, 335.
    • (1997) J. Heterocycl. Chem. , vol.34 , pp. 349
    • Simon, C.1    Sandor, H.2    Sandor, M.3
  • 12
    • 0000414496 scopus 로고
    • For review, see: (a) Mitsunobu, O. Synthesis 1981, 1-28. (b) Simon, C.; Sandor, H.; Sandor, M. J. Heterocycl. Chem. 1997, 34, 349. (c) Hughes, D. L. Org. Reactions 1992, 42, 335.
    • (1992) Org. Reactions , vol.42 , pp. 335
    • Hughes, D.L.1
  • 13
    • 33845550147 scopus 로고
    • (a) For the preparation and use of cross-linked polystyrene-supported triphenylphosphine, see: Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326-332.
    • (1983) J. Org. Chem. , vol.48 , pp. 326-332
    • Bernard, M.1    Ford, W.T.2
  • 30
    • 0011498790 scopus 로고
    • The synthesis and application of TAD on silica gel was reported; see: (1) Keana, J. F. W.; Ward, D. D. Synth. Commun. 1983, 13, 729-735. (2) Keana, J. F. W.; Guzikowski, A. P.; Ward, D. D.; Morat, C.; Van Nice, F. L. J. Org. Chem. 1983, 48, 2654-2660.
    • (1983) Synth. Commun. , vol.13 , pp. 729-735
    • Keana, J.F.W.1    Ward, D.D.2
  • 31
  • 32
    • 0141814450 scopus 로고    scopus 로고
    • note
    • The urazole 31 was successfully synthesized on polystyrene, and the loading was confirmed by elemental analysis to be 1.44 mmol/g. The oxidation of the polymer-supported urazole afforded a red resin, which is characteristic of the formation of TAD 32. Various oxidants and reaction conditions were tested, but none gave synthetically accessible loading of 32 higher than 0.4 mmol/g.
  • 33
    • 0141703056 scopus 로고    scopus 로고
    • note
    • (4-Maleimidobutyramidomethyl)polystyrene 11b was purchased from Fluka.
  • 34
    • 0141591331 scopus 로고    scopus 로고
    • note
    • -1, which is slightly higher than 11, presumably as a result of better accessibility of resin 11b. But because of the low loading, the time for >99% scavenging by resin 11b would be 24 h, instead of 13 h by resin 11, when the same condition was used (1 equiv anthracene-tagged compound 12, 1.2 equiv maleimide resin, and 10 mL solvent per gram of resin).
  • 38
    • 0030805612 scopus 로고    scopus 로고
    • Using HOBt as catalytic additive to promote the reaction between p-nitrophenyl carbonate and a very sluggish aziridine nitrogen nucleophile was reported before; see: Dubowchik, G. M.; King, H. D.; Pham-Kaplita, K. Tetrahedron Lett. 1997, 38, 5261-5264.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5261-5264
    • Dubowchik, G.M.1    King, H.D.2    Pham-Kaplita, K.3
  • 39
    • 0141591332 scopus 로고    scopus 로고
    • note
    • (a) Polystyrene-diethylenetriamine was custom ordered from Argonaut Technologies Inc., Lot no. 01264; loading, 2.63 mmol/g.
  • 42
    • 0141814449 scopus 로고
    • For example, see: (1) Medina, J. C.; Cadilla, R.; Kyler, K. S. Tetrahedron Lett. 1987, 1059-1062. (2) Kahn, M.; Wike, S.; Chen, B.; Fujita, K. J. Am. Chem. Soc. 1988, 110, 1638-1639.
    • (1987) Tetrahedron Lett. , pp. 1059-1062
    • Medina, J.C.1    Cadilla, R.2    Kyler, K.S.3
  • 43
    • 0000784430 scopus 로고
    • For example, see: (1) Medina, J. C.; Cadilla, R.; Kyler, K. S. Tetrahedron Lett. 1987, 1059-1062. (2) Kahn, M.; Wike, S.; Chen, B.; Fujita, K. J. Am. Chem. Soc. 1988, 110, 1638-1639.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1638-1639
    • Kahn, M.1    Wike, S.2    Chen, B.3    Fujita, K.4
  • 44
    • 0141701864 scopus 로고    scopus 로고
    • note
    • The "diethyl azodicarboxylate on polystyrene" from Fluka (Lot no: 12359/1 62502; loading, 1.2 mmol "N"/g) and the ethoxycarbonylazodicarboxymethyl polystyrene from Nova-biochem (Lot no. A27447; loading, 1.30 mmol/g). See Experimental Section for representative loadings.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.