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1
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7444228993
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Adapted from the Ph.D. Thesis of Burke, M. D., Harvard University, 2003
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Adapted from the Ph.D. Thesis of Burke, M. D., Harvard University, 2003.
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2
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0034678033
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(a) Schreiber, S. L. Science 2000, 287, 1964-1969.
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(c) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58 and references therein.
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(a) Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295-302 and references therein
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0142147275
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Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618 and references therein.
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Science
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Burke, M.D.1
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Schreiber, S.L.3
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Achmatowicz, O., Jr.; Bukowski, P.; Szechner, B.; Zwierzchowska, Z.; Zamojski, A. Tetrahedron 1971, 27, 1973-1996.
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Achmatowicz Jr., O.1
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0000510466
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Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63, 7505-7515.
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Kobayashi, Y.1
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0032506560
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Yang, C.-F.; Xu, Y.-M.; Liao, L.-X.; Zhou, W.-S. Tetrahedron Lett. 1998, 39, 9227-9228.
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Yang, C.-F.1
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13
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0033044961
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Takeuchi, M.; Taniguchi, T.; Ogasawara, K. Synthesis 1999, 2, 341-354.
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Takeuchi, M.1
Taniguchi, T.2
Ogasawara, K.3
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14
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0021248286
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Martin, S. F.; Gluchowski, C.; Campbell, C. L.; Chapman, R. C. J. Org. Chem. 1984, 49, 2512-2513.
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Martin, S.F.1
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15
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0021074524
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Deshong, P.; Ramesh, S.; Perez, J. J. J. Org. Chem. 1983, 48, 2117-2118.
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Deshong, P.1
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17
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0030884126
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Wender, P. A.; Rice, K. D.; Schnute, M. E. J. Am. Chem. Soc. 1997, 119, 7897-7898.
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Wender, P.A.1
Rice, K.D.2
Schnute, M.E.3
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19
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7444248803
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Cambridge, MA, March
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Burke, M. D.; Schreiber, S. L. Harvard-MIT Division of Health Sciences and Technology Forum, The Speech Chain, Book of Abstracts; Cambridge, MA, March, 2000; p 5.
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Harvard-MIT Division of Health Sciences and Technology Forum, The Speech Chain, Book of Abstracts
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Burke, M.D.1
Schreiber, S.L.2
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22
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0035351150
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(a) Tallarico, J. A.; Depew, K. M.; Pelish, H. E.; Westwood, N. J.; Lindsley, C. W.; Shair, M. D.; Schreiber, S. L.; Foley, M. A. J. Comb. Chem. 2001, 3, 312-318.
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(2001)
J. Comb. Chem.
, vol.3
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Tallarico, J.A.1
Depew, K.M.2
Pelish, H.E.3
Westwood, N.J.4
Lindsley, C.W.5
Shair, M.D.6
Schreiber, S.L.7
Foley, M.A.8
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23
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7444232958
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note
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(b) M. Narovlyansky and J. Tallarico are gratefully acknowledged for generously providing all of the macrobeads used in these studies.
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24
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4444276636
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(a) Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
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Chem. Rev.
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Kolb, H.C.1
Van Nieuwenhze, M.S.2
Sharpless, K.B.3
-
25
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0030824025
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(b) For a study of the Sharpless dihydroxylation on solid phase, see: Han, H.; Janda, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 1731-1733.
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(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
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Han, H.1
Janda, K.2
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26
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7444227859
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note
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In a solution-phase model study, the asymmetric dihydroxylation of a related substrate proceeded with >90% ee. It is unclear why the enantioselectivity was diminished for the solid-phase reaction.
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27
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0012016624
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Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
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(1981)
J. Am. Chem. Soc.
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Evans, D.A.1
Bartroli, J.2
Shih, T.L.3
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28
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7444226704
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note
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214) of crude products following cleavage from macrobeads.
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29
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7444220995
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note
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1H NMR-silent and had an isotope pattern in its mass spectrum consistent with an osmium-containing substance was not included in the calculation of the purity of product 35.
-
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-
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30
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7444219862
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-
note
-
1H NMR nOe studies) likely represents the thermodynamic product (minimization of sterics).
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31
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0023771943
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This reagent was purchased from Moscow MedChemlabs (Moscow, Russia) or synthesized in one step via treatment of 2-furaldehyde with molecular bromine in the presence of aluminum trichloride: Chiarello, J.; Joullié, M. M. Tetrahedron 1988, 44, 41-48.
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(1988)
Tetrahedron
, vol.44
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Chiarello, J.1
Joullié, M.M.2
-
32
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0037866299
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Similar regioselective Sonogashira and Stille couplings have been reported: Bach, T.; Krüger, L. Eur. J. Org. Chem. 1999, 2045-2057.
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(1999)
Eur. J. Org. Chem.
, pp. 2045-2057
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Bach, T.1
Krüger, L.2
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33
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33750283011
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(a) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314-321.
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J. Am. Chem. Soc.
, vol.111
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Miyaura, N.1
Ishiyama, T.2
Sasaki, H.3
Ishikawa, M.4
Satoh, M.5
Suzuki, A.6
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34
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0000488020
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(b) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
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Am. Chem. Soc.
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Hayashi, T.1
Konishi, M.2
Kobori, Y.3
Kumada, M.4
Higuchi, T.5
Hirotsu, K.J.6
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35
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0035912363
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Blackwell, H. E.; Clemons, P. A.; Schreiber, S. L. Org. Lett. 2001, 3, 1185-1188.
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(2001)
L. Org. Lett.
, vol.3
, pp. 1185-1188
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Blackwell, H.E.1
Clemons, P.A.2
Schreiber, S.3
-
37
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0000237691
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(b) Zhou, X.; Tse, M. K.; Wan, T. S. M.; Chan. K. S. J. Org. Chem. 1996, 61, 3590-3593.
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(1996)
J. Org. Chem.
, vol.61
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Zhou, X.1
Tse, M.K.2
Wan, T.S.M.3
Chan, K.S.4
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38
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7444247177
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note
-
2 in DMA at 115°C, two cycles].
-
-
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39
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7444261204
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-
note
-
The HWE olefination, reduction, functionalization, and dihydroxylation sequence was also explored with these and related substrates; however, the length of the synthesis pathway precluded the generation of the desired macrobead-bound diols with acceptable macrobead integrity and compound purity.
-
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40
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7444227297
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-
note
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The stereochemistry at the anomeric carbon of cyclic ketal 46 was tentatively assigned as R on the basis of two-dimensional NOESY and one-dimensional nOe experiments.
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42
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33947459206
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(b) Swern, D. Chem. Rev. 1949, 45, 1-68.
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(1949)
Chem. Rev.
, vol.45
, pp. 1-68
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Swern, D.1
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45
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0003791302
-
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Plenum Press: New York
-
(b) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd ed.; Plenum Press: New York, 1990; p 15.
-
(1990)
Advanced Organic Chemistry, Part A: Structure and Mechanisms, 3rd Ed.
, pp. 15
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Carey, F.A.1
Sundberg, R.J.2
-
47
-
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7444230804
-
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note
-
(a) Epimerization of the potentially labile methyl-bearing stereogenic center in 49 was not observed. This observation is consistent with the lack of epimerization observed with the structurally similar Evans' extended polypropionate (β-ketoimide) reagents.
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-
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48
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0025364262
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(b) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 866-868
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Evans, D.A.1
Clark, J.S.2
Metternich, R.3
Novack, V.J.4
Sheppard, G.S.5
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49
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0026553351
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(c) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127-2142.
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(1992)
Tetrahedron
, vol.48
, pp. 2127-2142
-
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Evans, D.A.1
Ng, H.P.2
Clark, J.S.3
Rieger, D.L.4
-
50
-
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7444236864
-
-
note
-
The olefin geometry was determined via nOe studies.
-
-
-
-
51
-
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2742513412
-
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Similar distinct stereochemical outcomes have been observed in the oxidation of an alternative series of furan derivatives: Sayama, S.; Inamura, Y. Heterocycles 1996, 43, 1371-1374.
-
(1996)
Heterocycles
, vol.43
, pp. 1371-1374
-
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Sayama, S.1
Inamura, Y.2
-
52
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7444241827
-
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note
-
Upon prolonged treatment with acidic reagents, slow degradation of 50 to unidentified byproducts was observed (this degradation was more rapid with CSA than with PPTS).
-
-
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53
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0031450710
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For a related bromination, see: Sessler, J. L.; Hoehner, M. C.; Gebauer, A.; Andrievsky, A.; Lynch, V. J. Org. Chem. 1997, 62, 9251-9260.
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(1997)
J. Org. Chem.
, vol.62
, pp. 9251-9260
-
-
Sessler, J.L.1
Hoehner, M.C.2
Gebauer, A.3
Andrievsky, A.4
Lynch, V.5
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54
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33751157590
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(a) Nestler, H. P.; Bartlett, P. A.; Still, W. C. J. Org. Chem. 1994, 59, 4723-4724.
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(1994)
J. Org. Chem.
, vol.59
, pp. 4723-4724
-
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Nestler, H.P.1
Bartlett, P.A.2
Still, W.C.3
-
55
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0035542849
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(b) Blackwell, H. E; Pérez, L.; Stavenger, R. A.; Tallarico, J. A.; Eatough, E. C.; Foley, M. A.; Schreiber, S. L. Chem. Biol. 2001, 8, 1167-1182.
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(2001)
Chem. Biol.
, vol.8
, pp. 1167-1182
-
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Blackwell, H.E.1
Pérez, L.2
Stavenger, R.A.3
Tallarico, J.A.4
Eatough, E.C.5
Foley, M.A.6
Schreiber, S.L.7
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56
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7444241246
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note
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Jennifer Raggio, Leticia Castro, and John Tallarico are gratefully acknowledged for providing encoding reagents, and for cleaving and analyzing chemical tags.
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-
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57
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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: Burgess, K.; Liaw, A. I.; Wang, N. J. Med. Chem. 1994, 37, 2985-2987.
-
(1994)
J. Med. Chem.
, vol.37
, pp. 2985-2987
-
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Burgess, K.1
Liaw, A.I.2
Wang, N.3
-
58
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7444228992
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note
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Throughout the course of the synthesis, the total mass of macrobeads increased somewhat, reflecting the added mass of the attached compounds. There was also some loss of intact macrobeads throughout the split-pool synthesis due to bead-breakage.
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