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15
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0142204879
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note
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Because split-pool synthesis involves the pooling of resin-bound reaction products after each step, it is not possible to optimize reaction conditions ad hoc for each compound in subsequent transformations.
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18
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0001462758
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21
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22
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0142173783
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note
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Materials and Methods are available as supporting online material on Science Online.
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25
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0037866299
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For a related regioselective Pd-mediated coupling with 4,5-dibromofuraldehyde, see T. Bach, L. Krüger [Eur. J. Org. Chem. 9, 2045 (1999)].
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Bach, T.1
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26
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0142142944
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note
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1H NMR nuclear Overhauser enhancement experiments.
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27
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0002437541
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For related acid-mediated rearrangements of sugars into α-keto furans see F. H. Newth [Adv. Carbohydrate Chem. 6, 83 (1951)]. Epimerization of the potentially labile stereogenic center in 18 was not observed.
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Newth, F.H.1
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28
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0142173782
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note
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See supporting information (22) for more computational details.
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30
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0028135116
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Statistical calculations and computer simulations suggest that a multiplicative factor of 3.1 is required to provide 99% confidence of achieving 95% coverage of the complete, theoretical combinatorial matrix for a split-pool synthesis involving four split-pool cycles with 10 pools per cycle [K. Burgess, A. I. Liaw, and N. Wang. J. Med. Chem. 37, 2985 (1994)].
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J. Med. Chem.
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Burgess, K.1
Liaw, A.I.2
Wang, N.3
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31
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0142235820
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note
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1HNMR-silent and had an isotope pattern in its mass spectrum consistent with an osmium-containing substance,was not included in calculating the purity of product 8.
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32
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0142142942
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note
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We gratefully acknowledge M. Narovlyansky for providing macrobeads 1; Q. Liao, P. Wang, and J. Dudek for HRMS analysis; J. Raggio, L. Castro, and J. Tallarico for providing encoding reagents and for cleaving and analyzing chemical tags; Y.-K. Kim for helpful discussions regarding the transformation of 3 → 4; and M. Kanan for thoughtful review of this manuscript. Supported by the NIGMS and the NCI. S.L.S. is an investigator at the Howard Hughes Medical Institute at Harvard. M.D.B. is an HHMI predoctoral fellow, and E.M.B. is an HHMI undergraduate fellow.
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