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7
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0035542853
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P.A. Clemons, A.N. Koehler, B.K. Wagner, T.G. Sprigings, D.R. Spring, R.W. King, S.L. Schreiber, and M.A. Foley Chem. Biol. 8 2001 1183 1195
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Spring, D.R.5
King, R.W.6
Schreiber, S.L.7
Foley, M.A.8
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8
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0035542849
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H.E. Blackwell, L. Perez, R.A. Stavenger, J.A. Tallarico, E.C. Eatough, M.A. Foley, and S.L. Schreiber Chem. Biol. 8 2001 1167 1182
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Blackwell, H.E.1
Perez, L.2
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Tallarico, J.A.4
Eatough, E.C.5
Foley, M.A.6
Schreiber, S.L.7
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16
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20344394518
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note
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MPEG-OH, HM resin, and SynPhase™ Lanterns were purchased from Aldrich Co. (catalog no. 20251-7), Advanced ChemTech, Inc. (catalog no. SA5020), and Mimotopes Pty Ltd (catalog no. SP-PS-L-HOM-015), respectively
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17
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20344402643
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note
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Polymers were recovered after the reactions by precipitation using diethyl ether for the liquid-phase synthesis, and by a simple washing in a stopcock-connected column for the solid-phase synthesis
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18
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20344388632
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note
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A stepwise reaction comprising acylation with bromoacetic acid followed by nucleophilic addition of phenol-type nucleophile is also effective. For the synthesis of 3B (MPEG) and 3C (HM resin), the loading proceeded in good yield (89%) and in poor yield (25%), respectively. The low yields are due to low reactivity of phenols toward alkyl bromide on the cross-linked polymer. Since various derivatives can be commercially available for phenol, we are now investigating high yield loading procedure via nucleophilic addition of phenol derivatives
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19
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0037427332
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As can be seen in run 1, (2-naphthyloxy)acetyl group is potentially useful for an efficient protecting group of hydroxy functionality. For phenoxyacetyl group for protection of secondary alcohol, see; K. Shimada, Y. Kaburagi, and T. Fukuyama J. Am. Chem. Soc. 125 2003 4048 4049
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J. Am. Chem. Soc.
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, pp. 4048-4049
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Shimada, K.1
Kaburagi, Y.2
Fukuyama, T.3
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20
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20344392517
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note
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2, the cleavage in various solvents is under investigation
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21
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20344392273
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note
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2, allylamine, ethylenediamine, and piperidine were also effective for the cleavage
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23
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3843054801
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M. Shoda, T. Harada, Y. Kogami, R. Tsujita, H. Akashi, H. Kouji, F.L. Stahura, L. Xue, and J. Bajorath J. Med. Chem. 47 2004 4286 4290
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Shoda, M.1
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Akashi, H.5
Kouji, H.6
Stahura, F.L.7
Xue, L.8
Bajorath, J.9
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25
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0034768614
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G.A. Pinna, G. Loriga, G. Murineddu, G. Grella, M. Mura, L. Vargiu, C. Murgioni, and P. La Colla Chem. Pharm. Bull. 49 2001 1406 1411
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Pinna, G.A.1
Loriga, G.2
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Grella, G.4
Mura, M.5
Vargiu, L.6
Murgioni, C.7
La Colla, P.8
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26
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0031661388
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A solution-phase Ugi-type three-component coupling reaction using perchloric acid has been reported, see; H. Bienayme, and K. Bouzid Angew. Chem., Int. Ed. 37 1998 2234 2237
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Bienayme, H.1
Bouzid, K.2
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