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Volumn 6, Issue 4, 2004, Pages 584-595

Automated flow-through synthesis of heterocyclic thioethers

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; RESIN; THIOL DERIVATIVE;

EID: 4143050396     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0499486     Document Type: Article
Times cited : (31)

References (48)
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    • For example, see: (a) Carpanone: Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1, 2002, 1850. (b) Plicamine: Baxendale, I. R.; Ley, S. V.; Nessi M.; Piutti, C. Tetrahedron 2002, 6285. (c) Epothilone: Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 2521. (d) Glycoconjugates: Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 1850
    • Baxendale, I.R.1    Lee, A.-L.2    Ley, S.V.3
  • 15
    • 0037025957 scopus 로고    scopus 로고
    • For example, see: (a) Carpanone: Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1, 2002, 1850. (b) Plicamine: Baxendale, I. R.; Ley, S. V.; Nessi M.; Piutti, C. Tetrahedron 2002, 6285. (c) Epothilone: Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 2521. (d) Glycoconjugates: Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166.
    • (2002) Tetrahedron , pp. 6285
    • Baxendale, I.R.1    Ley, S.V.2    Nessi, M.3    Piutti, C.4
  • 16
    • 0038001604 scopus 로고    scopus 로고
    • For example, see: (a) Carpanone: Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1, 2002, 1850. (b) Plicamine: Baxendale, I. R.; Ley, S. V.; Nessi M.; Piutti, C. Tetrahedron 2002, 6285. (c) Epothilone: Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 2521. (d) Glycoconjugates: Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 2521
    • Storer, R.I.1    Takemoto, T.2    Jackson, P.S.3    Ley, S.V.4
  • 17
    • 0037429819 scopus 로고    scopus 로고
    • For example, see: (a) Carpanone: Baxendale, I. R.; Lee, A.-L.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1, 2002, 1850. (b) Plicamine: Baxendale, I. R.; Ley, S. V.; Nessi M.; Piutti, C. Tetrahedron 2002, 6285. (c) Epothilone: Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem., Int. Ed. 2003, 42, 2521. (d) Glycoconjugates: Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem., Int. Ed. 2003, 42, 1166.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1166
    • Jaunzems, J.1    Hofer, E.2    Jesberger, M.3    Sourkouni-Argirusi, G.4    Kirschning, A.5
  • 32
    • 0032080369 scopus 로고    scopus 로고
    • -1, see: Schwesinger, R. Chimia 1985, 39, 269. For an example of the use of this base in alkylation of acidic heterocycles, see: Xu, W.; Mohan, R.; Morrissey, M. M. Bioorg. Med. Chem. Lett. 1998, 8, 1089.
    • (1985) Chimia , vol.39 , pp. 269
    • Schwesinger, R.1
  • 33
    • 0032080369 scopus 로고    scopus 로고
    • -1, see: Schwesinger, R. Chimia 1985, 39, 269. For an example of the use of this base in alkylation of acidic heterocycles, see: Xu, W.; Mohan, R.; Morrissey, M. M. Bioorg. Med. Chem. Lett. 1998, 8, 1089.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1089
    • Xu, W.1    Mohan, R.2    Morrissey, M.M.3
  • 34
    • 0030767571 scopus 로고    scopus 로고
    • -1: (a) Morrissey, M. M.; Mohan, R.; Xu, W. Tetrahedron Lett. 1997, 38, 7337. (b) Organ, M. G.; Dixon, C. E. Biotech. Bioeng. Comb. Chem. 2000, 71, 71.
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    • Morrissey, M.M.1    Mohan, R.2    Xu, W.3
  • 44
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    • note
    • Commercial Gilson HPLC modules were used to construct the flow-through synthesiser, and the device was controlled using Unipoint v3.3 software (www.Gilson.com).
  • 45
    • 4143080894 scopus 로고    scopus 로고
    • note
    • Although in principle, slope detection can also be used to control the fraction collector, this method was found to be unreliable in this case.
  • 46
    • 4143093155 scopus 로고    scopus 로고
    • note
    • In principle, according to the flow-through paradigm we have exploited, compounds with high purities should also be associated with high isolated yields. Lower yields would be expected to correlate to products that were contaminated with unreacted alkylating agent, particularly for nonvolatile electrophiles. However, this was not observed in practice, and all purities were uniformly high. The lower yields are most likely to be attributable to nonoptimal sample collection in some cases, which arises as a consequence of using a generic set of parameters to trigger the fraction collector.


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