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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.
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0038001604
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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.
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Angew. Chem., Int. Ed.
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Storer, R.I.1
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Ley, S.V.4
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0037429819
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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.
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Jaunzems, J.1
Hofer, E.2
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For an example of how this may be achieved by a divergent solid-phase synthesis, see: Purandare, A. V.; Aiming, G.; Poss, M. A. Tetrahedron Lett. 2002, 43, 3903.
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44
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note
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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).
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45
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note
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Although in principle, slope detection can also be used to control the fraction collector, this method was found to be unreliable in this case.
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46
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4143093155
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note
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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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