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Volumn 62, Issue 16, 1997, Pages 5615-5618

Solid-phase synthesis via 5-oxazolidinones. Ring-opening reactions with amines and reaction monitoring by single-bead FT-IR microspectroscopy

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINONE DERIVATIVE;

EID: 0030811387     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9623503     Document Type: Article
Times cited : (18)

References (47)
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    • Grant, G. A., Ed.; W. H. Freeman: New York
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1992) Synthetic Peptides: A Users Guide , pp. 77
    • Fields, G.B.1    Tian, Z.2    Barany, G.3
  • 3
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    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3045-3046
    • Letsinger, R.L.1    Kornet, M.J.2
  • 4
    • 0026606239 scopus 로고
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1992) Tetrahedron , vol.48 , pp. 2223-2311
    • Beaucage, S.L.1    Iyer, R.P.2
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    • 0002454833 scopus 로고
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1974) Chem. Soc. Rev. , pp. 65-85
    • Lenznoff, C.C.1
  • 6
    • 0009470488 scopus 로고
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1974) Acc. Chem. Res. , vol.11 , pp. 327-333
    • Leznoff, C.C.1
  • 7
    • 33748237769 scopus 로고    scopus 로고
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 17-42
    • Früchtel, J.S.1    Jung, G.2
  • 8
    • 7044263277 scopus 로고    scopus 로고
    • Peptides: (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154. (b) Fields, G. B.; Tian, Z.; Barany, G. In Synthetic Peptides: A Users Guide; Grant, G. A., Ed.; W. H. Freeman: New York, 1992; p 77. Oilgonucleotides: (c) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045-3046. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311. (e) Lenznoff, C. C. Chem. Soc. Rev. 1974, pp 65-85. (f) Leznoff, C. C. Acc. Chem. Res. 1974, 11, 327-333. (g) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (h) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
    • (1996) Chem. Rev. , vol.96 , pp. 555-600
    • Thompson, L.A.1    Ellman, J.A.2
  • 42
    • 0025900609 scopus 로고
    • -1 was distinctly observed on amino methyl resin when SCAL linker (Pátek, M.; Lebl, M. Tetrahedron Lett. 1991, 32, 3891-3894) was used (data not shown).
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3891-3894
    • Pátek, M.1    Lebl, M.2
  • 44
    • 8544225449 scopus 로고    scopus 로고
    • note
    • We are unable to extract coupling constants for the allylic protons as they are overlapped with the proton of the oxazolidinone.
  • 45
    • 8544272218 scopus 로고    scopus 로고
    • note
    • Solid-phase-resin reactions were mixed by nitrogen sparge through sintered glass fritted reaction vessels.


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