The combinatorial index:
"Combinatorial chemistry has become a major focus of research activity for pharmaceutical, agrochemical, and biotechnology companies. The explosion of combinatorial methods has created the need for a compendium of reliable synthetic transformations from the primary literature. The Combinatorial...
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
San Diego [u.a.]
Acad. Press
1998
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Zusammenfassung: | "Combinatorial chemistry has become a major focus of research activity for pharmaceutical, agrochemical, and biotechnology companies. The explosion of combinatorial methods has created the need for a compendium of reliable synthetic transformations from the primary literature. The Combinatorial Index fills this need. Included are chapters on linkers, solid-phase synthetic methods, analytical techniques, and solution libraries. Procedures from the literature for constructing combinatorial libraries of small molecules comprise an indispensable laboratory reference for the synthetic chemist. Each procedure in the compilation is preceded by a section entitled "Points of Interest," which highlights the strengths and limitations of the various methods. A structural appendix covers both functional group transformations and heterocyclization reactions in solid-phase synthesis. This comprehensive but easy-to-access guide to the combinatorial chemistry literature will save time on tedious library searches, introduce a growing audience of chemists to this exciting field, and lower the barriers to attempting a new or related methodology."--BOOK JACKET. |
| Beschreibung: | XVII, 322 S. Ill. |
| ISBN: | 0121413403 |
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| 520 | 1 | |a "Combinatorial chemistry has become a major focus of research activity for pharmaceutical, agrochemical, and biotechnology companies. The explosion of combinatorial methods has created the need for a compendium of reliable synthetic transformations from the primary literature. The Combinatorial Index fills this need. Included are chapters on linkers, solid-phase synthetic methods, analytical techniques, and solution libraries. Procedures from the literature for constructing combinatorial libraries of small molecules comprise an indispensable laboratory reference for the synthetic chemist. Each procedure in the compilation is preceded by a section entitled "Points of Interest," which highlights the strengths and limitations of the various methods. A structural appendix covers both functional group transformations and heterocyclization reactions in solid-phase synthesis. This comprehensive but easy-to-access guide to the combinatorial chemistry literature will save time on tedious library searches, introduce a growing audience of chemists to this exciting field, and lower the barriers to attempting a new or related methodology."--BOOK JACKET. | |
| 650 | 7 | |a Chimie combinatoire |2 ram | |
| 650 | 7 | |a Combinatorische chemie |2 gtt | |
| 650 | 7 | |a Composés organiques - Synthèse |2 ram | |
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Datensatz im Suchindex
| _version_ | 1804128035274752000 |
|---|---|
| adam_text | IMAGE 1
THE
COMBINATORIAL INDEX
BARRY A. BUNIN ARRIS PHARMACEUTICAL SAN FRANCISCO, CALIFORNIA
ACADEMIC PRESS
SAN DIEGO LONDON BOSTON NEW YORK SYDNEY TOKYO TORONTO
IMAGE 2
CONTENTS
FOREWORD XV ACKNOWLEDGMENTS XVII 1 INTRODUCTION I
2 BACKGROUND 5
3 LINKERS FOR SOLID-PHASE SYNTHESIS 9
3.1 RESIN DERIVATIZATION 11 3.1.1 BROMINATION AND LITHIATION: TWO
IMPORTANT STEPS IN THE FUNCTIONALIZATION OF POLYSTYRENE RESINS 12 3.1.2
ZINC CHLORIDE-CATALYZED CHLORONTETHYLATION OF RESINS FOR
SOLID-PHASE PEPTIDE SYNTHESIS 13 3.1.3 HIGH-CAPACITY
(AMINOTNETHYL)POLYSTYRENE RESIN 14 3.2 LINKERS FOR CARBOXYLIC ACIDS 15
3.2.1 GLYCOLAMIDIC ESTER LINKER 17
3.2.2 SHEPPARD S LINKERS FOR FMOC-AMINO ACID SYNTHESIS 18 3.2.3 PAM
LINKER: PHENYLACETAMIDOMETHYL (PAM) RESIN 19
IMAGE 3
VI
CONTENTS
3.2.4 TERT-BUTYL RESIN: 4-{L ,1 -DIMETHYL-1 -
HYDROXYPROPYLFPHENOXYACETYL (DHPP) HANDLE 20 3.2.5 WANG LINKER: P-ALKOXY
BENZYL ALCOHOL RESIN 21 3.2.6 SASRIN (SUPER ACID SENSITIVE RESIN) 22
3.2.7 HYPERSENSITIVE ACID-LABILE (HAL) TRIS(ALKOXY)BENZYL ESTER ANCHOR
23 3.2.8 2-CHLOROTRITYL CHLORIDE RESIN 24 3.2.9 RINK ESTER AND AMIDE
RESINS 25 3.2.10 SAC (SILYL ADD) LINKER 26 3.2.11 BARANY S PBS LINKER 27
3.2.12 RAMAGE S SILYL LINKERS 28 3.2.13 THE FIRST O-NITROBENZYI RESIN
FOR SOLID-PHASE SYNTHESIS OF
BOC-PEPTIDE ACIDS 28 3.2.14 A-METHYLPHENACYL ESTER LINKER 29 3.2.15
REDUCTIVE ACIDOLYSIS SAFETY-CATCH LINKER 31 3.2.16 SAFETY-CATCH LINKER
CLEAVED BY INTRAMOLECULAR ACTIVATION 31
3.2.17 SAFETY-CATCH LINKAGE FOR THE DIRECT RELEASE INTO AQUEOUS BUFFERS
33 3.2.18 ALLYLIC LINKERS 34 3.2.19 FLUORENE-DERIVED LINKER:
N-[9-(HYDROXYMETHYL)-2-
FLUORENYLJSUCCINAMIC ACID (HMFS) HANDLE 35 3.2.20 BASE-LABILE LINKER:
FOR CLEAVAGE VIA ^-ELIMINATION 35 3.2.21 AN OXIDATION-LABILE LINKER 36
3.3 LINKERS FOR AMIDES 37
3.3.1 RINK ESTER AND AMIDE RESINS 38 3.3.2 PAL LINKER:
FMOC-(AMINOMETHYL)~3 5- DIMETHOXYPHENOXYVALERIC ACID (PAL) RESIN 39
3.3.3 CHA AND CHE LINKERS 40
3.3.4 9-XANTHENYL (XAN) LINKER: FOR CLEAVAGE OFPEPTIDE AMIDES BY VERY
MILD ACIDOLYSIS 41 3.3.5 SAL (SILYL AMIDE LINKER) 42 3.3.6 PHOTOLABILE
AMIDE LINKERS 42
3.3.7 A NEW O-NITROBENZYL PHOTOLABILE LINKER FOR COMBINATORIAL SYNTHESIS
43 3.3.8 N-METHYL- AND N-ETHYLAMIDES OFPEPTIDES 44 3.3.9 OXIDATIVE
PHENOL-SULFIDE SAFETY-CATCH LINKER 46 3.3.10 KENNER S SAFETY-CATCH
LINKER 47 3.3. 11 A HIGHLY REACTIVE ACYLSULFONAMIDE LINKER 48 3.3.12
SCAL (SAFETY-CATCH ACID-LABILE) LINKER 50 3.3.13 OXIME RESIN 50 3.4
LINKERS FOR ALCOHOLS AND AMINES 52
3.4.1 TRITYL RESINS: GENERAL INFORMATION 52 3.4.2 ORIGINAL STUDIES:
TRITYL RESINS FOR SYMMETRICAL BUT NOT A- OR P-POLYOLS 53 3.4.3 ORIGINAL
STUDIES: TRITYL AND HIGHLY CROSS-LINKED
TRITYL RESINS 54 3.4.4 TETRAHYDROPYRANYL (VHP) LINKER: FOR ALCOHOLS 55
IMAGE 4
CONTENTS VII
3.4.5 KETAL AND ACETAL LINKERS: FOR DIOLS AND ALCOHOLS 56
3.4.6 LINKERS FOR AMINES: A SOLID-PHASE CBZ CHLORIDE EQUIVALENT 58 3.4.7
SILYL CHLORIDE LINKERS FOR ALCOHOLS 59 3.4.8 LINKER FOR PREPARATION
OFC-TERMINAL PEPTIDE ALCOHOLS
(AND PEPTIDE ALDEHYDES) 60 3.4.9 SULFONATE ESTER LINKAGE FOR
OLIGOSACCHARIDE SYNTHESIS 61 3.4.10 LINKERS FOR AMINES: A SUPPORT-BOUND
P-NITROPHENYL CARBONATE 62 3.4.11 AN ADCC LINKER FOR PRIMARY AMINES 63
3.4.12 REM LINKER: FOR THE PREPARATION OF TERTIARY AMINES 64 3.5 LINKERS
FOR HYDROCARBONS AND OTHER FUNCTIONAL GROUPS 65 3.5.1 TRACELESS SILYL
LINKERS: FOR THE PREPARATION OF 1,4-BENZODIAZEPINES 66
3.5.2 PROTIODETACHABLE ARYLSILANE LINKER: FOR THE PREPARATION OFBIARYLS
67 3.5.3 SILICON-DIRECTED IPSO SUBSTITUTION OF POLYMER- BOUND
ARYLSILANES 68 3.5.4 A SILYL ETHER LINKER FOR SOLID-PHASE ORGANIC
SYNTHESIS 69 3.5.5 PHOSPHONIUM SALTS AS TRACELESS SUPPORTS FOR SOLID-
PHASE SYNTHESIS 70 3.5.6 A NOVEL 3-PROPYL-3-(BENZYL~SUPPORTED)TRIAZINE
LINKAGE FOR THE SOLID-PHASE SYNTHESIS OF PHENYLACETYLENE OLIGOMERS 71
3.5.7 REISSERT-BASED TRACELESS AMIDE LINKAGE TO SUPPORT 73 3.5.8
THIOESTER LINKER FOR THE PREPARATION OFTHHACIDS 73 3.5.9 DISULFIDE
LINKER FOR SOLID-PHASE SYNTHESIS 74 3.5.10 LINKAGES FOR OTHER FUNCTIONAL
GROUPS 76
4 COMBINATORIAL SOLID-PHASE SYNTHESIS 77
4.1 CONDENSATIONS TO PREPARE AMIDES, ESTERS, UREAS, IMINES, AND
PHOSPHORUS COMPOUNDS 77 4.1.1 AMIDE BOND FORMATION 78 4.1.2
ESTERIFICATION REACTIONS ON SOLID SUPPORT: FIRST AMINO ACID
LOADING BY ESTER BOND FORMATION 82 4.1.3 IMINE FORMATION ON SOLID
SUPPORT 84 4.1.4 UREA FORMATION ON SOLID SUPPORT: A STRATEGY FOR
COMBINATORIAL SOLID-PHASE SYNTHESIS AT UREA-LINKED DIAMINE LIBRARIES 86
4.1.5 CONDENSATIONS WITH PHOSPHORUS COMPOUNDS ON SOLID SUPPORT 87 4.2
CARBON-CARBON BOND FORMATION ON SOLID SUPPORT 90 4.2.1 SUZUKI REACTIONS
ON SOLID SUPPORT 91
4.2.2 ORGANOZINC REACTIONS ON SOLID SUPPORT: ZINC ORGANIC REAGENTS IN
ARYL-ARYL CROSS-COUPLING ON SOLID SUPPORT 94 4.2.3 STHLE COUPLING
REACTIONS ON SOLID SUPPORT 95 4.2.4 HECK REACTIONS ON SOLID SUPPORT 96
IMAGE 5
CONTENTS
4.2.5 ENOLATE ALKYLATION FOR CARBON-CARBON BOND FORMATION ON
SOLID SUPPORT 98 4.2.6 SOLID-PHASE WITTIG REACTIONS 102 4.2.7 METATHESIS
REACTIONS ON SOLID SUPPORT 104 4.2.8 OTHER EXAMPLES OF CARBON-CARBON
BOND FORMATION ON
SOLID SUPPORT 105
A3 MITSUNOBU REACTIONS ON SOLID SUPPORT 106 4.3.1 AN EFFICIENT
SOLID-PHASE MITSUNOBU REACTION IN THE PRESENCE OF A TERTIARY AMINE 106
4.3.2 SOLID-PHASE SYNTHESIS OFARYL ETHERS VIA THE
MITSUNOBU REACTION 107 4.3.3 POLYMER-SUPPORTED MITSUNOBU ETHER FORMATION
AND ITS USE IN COMBINATORIAL CHEMISTRY 108 4.3.4 MITSUNOBU
FUNCTIONALIZATION OF BIPHENYL PHENOLS 108 4.3.5 THE SOLID-PHASE
SYNTHESIS OF PHOSPHONIC ACID ESTERS UNDER
MODIFIED MITSUNOBU CONDITIONS 109 4.3.6 MITSUNOBU COUPLING WITH A
SUPPORT- BOUND TRIFLUOROANILIDE 110 4.3.7 ADDITIONAL STUDIES OF
MITSUNOBU REACTIONS ON
SOLID SUPPORT 111
4.4 SUBSTITUTION AND ADDITION REACTIONS ON SOLID SUPPORT 112 4.4.1
NUCLEOPHILIC DISPLACEMENT OF SUPPORT-BOUND A-BROMO AMIDES IN THE
SUBMONOMER PREPARATION OFPEPTOIDS 112 A A.I THIOL ALKYLATION IN THE
SOLID-PHASE SYNTHESIS OF
FI-TURN MIMETICS 113 4.4.3 ANILIDE ALKYLATION WITH PRIMARY ALKYL HALIDES
IN THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINES 115 A.A.A ONE-POT
CYCLIZATION AND ANILIDE ALKYLATION IN THE SOLID-PHASE
SYNTHESIS OF L,4-BENZODIAZEPINE-2,5-DIONES 116 4.4.5 SUCCESSIVE AMIDE
ALKYLATIONS: LIBRARIES FROM LIBRARIES 117 4.4.6 BENZOPHENONE IMINE
A-CARBON ALKYLATION IN SOLID-PHASE UNNATURAL PEPTIDE SYNTHESIS 118
4.4.7 ALKYLATION OR SULFONYLATION OF A SUPPORT-BOUND PHENOL 120 4.4.8
ENOLATE MONOALKYLATION FOR CARBON-CARBON BOND FORMATION ON SOLID SUPPORT
121 4.4.9 ALKYLATION OF SUPPORT-BOUND 1,3-DIKETONES IN THE SOLID-PHASE
SYNTHESIS OFPYRAZOLES AND ISOXAZOLES 122 4.4.10 TOSYL DISPLACEMENT WITH
PRIMARY OR SECONDARY AMINES ON SOLID SUPPORT 123 4.4.11 GRIGNARD
ADDITIONS TO SUPPORT-BOUND ESTERS 124 4.4.12 S N AR REACTION ON SOLID
SUPPORT 125 4.4.13 PALLADIUM-CATALYZED AMINATION OF RESIN-BOUND
AROMATIC BROMIDES 126 4.4.14 1,4-MICHAEL ADDITION OFTHIOLS TO
SUPPORT-BOUND ENONES 127 4.4.15 THE IODOETHERIFICATION REACTION IN THE
SOLID-PHASE SYNTHESIS OF
MICONAZOLE ANALOGS 128 4.4.16 REACTIONS WITH SUPPORT-BOUND ALKYL HALIDES
IN SOLID-PHASE PEPTIDE AND COMBINATORIAL SYNTHESIS 129
IMAGE 6
CONTENTS IX
4.5 OXIDATIONS ON SOLID SUPPORT 130
4.5.1 OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES 131 4.5.2 OXIDATION
OF (CHLOROMETHYL)POLYSTYRENE RESIN TO FORMYLPOLYSTYRENE AND
CARBOXYPOLYSTYRENE RESINS 132 4.5.3 OTHER EXAMPLES OF OXIDATION ON SOLID
SUPPORT 132 4.6 REDUCTIONS ON SOLID SUPPORT 133
4.6.1 RAPID OPTIMIZATION OF OXIDATION AND REDUCTION REACTIONS ON A SOLID
PHASE USING THE MULTIPIN APPROACH: SYNTHESIS OF 4-AMINOPROLINE ANALOGS
133
4.6.2 REDUCTIVE ALKYLATION ON A SOLID PHASE: SYNTHESIS OF A
PIPERAZINEDIONE COMBINATORIAL LIBRARY 134 4.6.3 REDUCTIVE ALKYLATION
OFSIEBER S XAN LINKER 135 4.6.4 LOADING AMINO ESTERS ONTO RESIN VIA
REDUCTIVE AMINATION 136 4.6.5 REDUCTIVE AMINATION OF A SUPPORT-BOUND
ANILINE 137 4.6.6 SOLID-PHASE REDUCTIVE ALKYLATION OF SECONDARY AMINES
USING
BORANE-PYRIDINE COMPLEX 138 4.6.7 REDUCTION OF SUPPORT-BOUND AMIDES WITH
RED-AL 138 4.6.8 REDUCTION OF SUPPORT-BOUND KETONES TO ALCOHOLS ON
PEG-PS 139
4.6.9 REDUCTION OF A SUPPORT-BOUND NITRO GROUP TO AN ANILINE 139 4.6.10
REDUCTION OF A SUPPORT-BOUND AZIDE TO AN AMINE 140 4.6.11 SOLID-PHASE
SYNTHESIS OF (R^-L-AMINOPHOSPHINIC ACIDS 141 4.6.12 ADDITIONAL STUDIES
OF REDUCTIONS ON SOLID SUPPORT 142 4.7 PREPARATION OF HETEROCYCLIC
COMPOUNDS 143
4.7.1 SYNTHESIS OF 1,4-BENZODIAZEPINES FROM SUPPORT-BOUND
2-AMINOBENZOPHENONES OR AMINOARYLSTANNANES 145 4.7.2 SOLID-PHASE
SYNTHESIS OF 1,4-BENZODIAZEPINES FROM SUPPORT- BOUND AMINO ESTERS 148
4.7.3 PREPARATION OF 1,4-BENZODIAZEPINE-2,5-DIONES FROM ANTHRANILIC
ACIDS 150 4.7.4 SOLID-PHASE SYNTHESIS OF L,4-BENZODIAZEPINE-2,5-DIONES
FROM SUPPORT-BOUND PEPTOIDS 152
4.7.5 SOLID-PHASE SYNTHESIS OFFI-TURN MIMETICS INCORPORATING SIDE CHAINS
154 4.7.6 EXPEDIENT SOLID-PHASE SYNTHESIS OF SECOND GENERATION {3-TURN
MIMETICS INCORPORATING THE I + 1, I + 2, AND I + 3
SIDE CHAINS 156 4.7.7 SOLID-PHASE SYNTHESIS OF HYDANTOINS USING A
CARBAMATE LINKER AND A NOVEL CYCLIZATIONICLEAVAGE STEP 158 4.7.8
SOLUTION- AND SOLID-PHASE SYNTHESIS OF
5-ALKOXY HYDANTOINS 159 4.7.9 POSTMODIFICATION OFPEPTOID SIDE CHAINS TO
ISOXAZOLES AND ISOXAZOLINES: [3 + 2} CYCLOADDITION OFNITRILE OXIDES WITH
ALKENES AND ALKYNES ON THE SOLID PHASE 160 4.7.10 SOLID-PHASE SYNTHESIS
OF PYRAZOTES AND ISOXAZOLES 162 4.7.11 SOLID-PHASE SYNTHESIS OF
STRUCTURALLY DIVERSE 1 -PHENYLPYRAZOLONE DERIVATIVES 163
IMAGE 7
CONTENTS
4.7.12 IMIDAZOLE LIBRARIES ON SOLID SUPPORT 164
4.7.13 TETRASUBSTITUTED IMIDAZOLES VIA A-N-ACYL-N-ALKYLAMINO-B-
KETOAMIDES 165 4.7.14 PYRROLES DERIVED FROM A FOUR-COMPONENT
CONDENSATION 166 4.7.15 REDUCTIVE ALKYLATION ON A SOLID PHASE: SYNTHESIS
OF A
PIPERAZINEDIONE COMBINATORIAL LIBRARY 167 4.7.16 SOLID-PHASE SYNTHESIS
OF DIKETOPIPERAZINES AND DIKETOMORPHOLINES 168 4.7.17 SOLID-PHASE
SYNTHESIS OF 2-OXOPIPERAZINES BY INTRAMOLECULAR
MICHAEL ADDITION 170 4.7.18 SOLID-PHASE SYNTHESIS OF 1 T
4-DIHYDROPYRIDINES 172 4.7.19 SOLID-PHASE SYNTHESIS OFPYRIDINES AND
PYRIDO [2,3-D] PYRIMIDINES 173 4.7.20 SOLID-PHASE PROTOCOL OF THE
BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS 174 4.7.21 SOLID-PHASE SYNTHESIS
OF 5,6-DIHYDROPYRIMIDINE-
2,4-DIONES 176 4.7.22 SOLID-PHASE SYNTHESIS OFDIHYDRO- AND
TETRAHYDROISOQUINOLINES 177 4.7.23 SOLID-PHASE SYNTHESIS OF HIGHLY
SUBSTITUTED PEPTOID 1 (2H)-
ISOQUINOLINES 178 4.7.24 SOLID-PHASE SYNTHESIS OF 2,6-DISUBSTITUTED
QUINOLINE DERIVATIVES 180 4.7.25 SOLID-PHASE SYNTHESIS
OF1,3-DIALKYLQUINAZOLINE-
2,4-DIONES 181 4.7.26 SOLID-PHASE SYNTHESIS OF 1,3-DISUBSTITUTED
2,4(1H,3H)-QUINAZOLINEDIONES 182 4.7.27 SOLID-PHASE SYNTHESIS OF
TETRAHYDROISOQUINOLINES AND
TETRAHYDROIMIDAZOPYRIDINES 184 4.7.28 A SOLID-PHASE APPROACH TO
QUINOLONES 184 4.7.29 SOLUTION AND POLYMER-SUPPORTED SYNTHESIS OF
4-THIAZOLIDMONES AND 4-METATHIAZANONES 186 4.7.30 SOLID-PHASE SYNTHESIS
OF THIAZOLIDINES 188 4.7.31 COMBINATORIAL SYNTHESIS OF HIGHLY
FUNCTIONALIZED PYRROLIDINES 189 4.7.32 SOLID-PHASE SYNTHESIS OFPROLINE
ANALOGS VIA A THREE-COMPONENT 1,3-DIPOLAR CYCLOADDITION 190 4.7.33
SOLID-SUPPORTED COMBINATORIAL SYNTHESIS OF/3-LACTAMS 192 4.7.34
DIHYDROBENZOPYRANS UTILIZING THE SPLIT SYNTHESIS METHOD AND THE
HALOAROMATIC TAG-ENCODING STRATEGY 194 4.7.35 BICYCLOF 2.2.2]OCTANE
DERIVATIVES VIA TANDEM MICHAEL ADDITION REACTIONS 195 4.7.36 SOLID-PHASE
SYNTHESIS OFTROPANE DERIVATIVES VIA A PALLADIUM-
MEDIATED THREE-COMPONENT COUPLING STRATEGY 197 4.7.37 SOLID-PHASE
SYNTHESIS OF AZABICYCLO[4.3.0}NONEN-8-ONE AMINO ACID DERIVATIVES VIA
INTRAMOLECULAR PAUSON- KHAND CYCLIZATION 199
IMAGE 8
CONTENTS XI
4.7.38 PICTET-SPENGLER REACTION ON AN OXIME RESIN: SYNTHESIS OF
1,2,3,4-TETRAHYDRO-FI-CARBOLINE LIBRARIES 200 4.7.39 PICTET-SPENGLER
REACTION ON A NITROPHENYL CARBONATE RESIN: SOLID-PHASE SYNTHESIS OF
1,2,3,4-TETRAHYDRO-F3-CARBOLINES 201 4.7.40 PICTET-SPENGLER REACTION ON
MERRIFIELD RESIN 202
4.7.41 PICTET-SPENGLER REACTION ON WANG RESIN 203 4.7.42 FISCHER INDOLE
SYNTHESIS ON SOLID SUPPORT 204 4.7A3 THE HECK REACTION IN THE
SOLID-PHASE SYNTHESIS OF INDOLE ANALOGS 206 A.7A4 SOLID-PHASE SYNTHESIS
OF OLOMOUCINE (PURINE) DERIVATIVES 207 4.7.45 SYNTHESIS OF AROMATIC
1,2-DIAZINES BY INVERSE ELECTRON DEMAND
DIELS-ALDER REACTION OF POLYMER-SUPPORTED 1 2,4,5- TETRAZINES 209 4.7.46
LIBRARY GENERATION THROUGH SUCCESSIVE SUBSTITUTION OF TRICHLOROTRIAZINE
210 4.7.47 OTHER EXAMPLES OF THE SOLID-PHASE SYNTHESIS
OF HETEROCYCLES 211
5 ANALYTICAL METHODS FOR SOLID-PHASE SYNTHESIS 213
5.1 COLORMETRIC ASSAYS ON SOLID SUPPORT 214 5.1.1 NINHYDRIN COLOR TEST
FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN THE SOLID-PHASE SYNTHESIS
OFPEPTIDES 214 5.1.2 QUANTITATIVE MONITORING OF SOLID-PHASE PEPTIDE
SYNTHESIS BY THE
NINHYDRIN REACTION 215 5.1.3 BROMOPHENOL BLUE TEST FOR NONINVASIVE,
CONTINUOUS DETECTION OF FREE AMINES 216 5.1.4 QUANTITATION OF AMINES
WITH THE PICRIC ACID TEST 217 5.1.5 NPITFOR QUANTITATIVELY MONITORING
REACTIONS OF AMINES IN
COMBINATORIAL SYNTHESIS 218 5.1.6 OTHER EXAMPLES OF COLORIMETRIC ASSAYS
ON SOLID SUPPORT 218 5.2 IDENTIFICATION OF COMPOUNDS RELEASED FROM RESIN
219 5.2.1 DMT QUANTITATION OF FREE AMINES OR ALCOHOLS 219
5.2.2 FMOC QUANTITATION 219 5.2.3 OTHER EXAMPLES OF THE IDENTIFICATION
OF COMPOUNDS RELEASED FROM RESIN 220 5.3 NMR TECHNIQUES FOR SOLID-PHASE
SYNTHESIS 220 5.3.1 APPLICATION OF GEL-PHASE N C NMR TO MONITOR
SOLID-PHASE
PEPTIDE SYNTHESIS 220 5.3.2 U CNMR RELAXATION TIMES OF A TRIPEPTIDE
METHYL ESTER AND ITS POLYMER-BOUND ANALOGS 221 5.3.3 REACTION MONITORING
BY GEL-PHASE P NMR 221 53 A I9 F NMR MONITORING OF AN S N AR REACTION
ON
SOLID SUPPORT 222 53.5 HIGH-RESOLUTION J H NMR IN SOLID-PHASE ORGANIC
SYNTHESIS 222
IMAGE 9
CONTENTS
5.3.6 MAS CH CORRELATION IN SOLVENT-SWOLLEN RESIN 223
5.3.7 UTILIZATION OF MAGIC-ANGLE-SPINNING HMQC AND TOCSY NMR SPECTRA IN
THE STRUCTURE DETERMINATION OF WANG-BOUND LYSINE 224
5.3.8 USE OF SPIN ECHO MAGIC-ANGLE-SPINNING L H NMR IN REACTION
MONITORING IN COMBINATORIAL ORGANIC SYNTHESIS 224 5.3.9 INFLUENCE OF
RESIN STRUCTURE, TETHER, LENGTH, AND SOLVENT UPON THE HIGH-RESOLUTION L
H NMR SPECTRA OF SOLID-PHASE
SYNTHESIS RESINS 225 5.3.10 AN NMR METHOD TO IDENTIFY NONDESTRUCTIVELY
CHEMICAL COMPOUND BOUND TO A SINGLE SOLID-PHASE SYNTHESIS BEAD FOR
COMBINATORIAL CHEMISTRY APPLICATIONS 226 5.3.11 A COMPARISON OF NMR
SPECTRA OBTAINED FOR SOLID-PHASE
SYNTHESIS RESINS USING CONVENTIONAL HIGH-RESOLUTION, MAGIC-
ANGLE-SPINNING, AND HIGH-RESOLUTION MAGIC-ANGLE- SPINNING PROBES 226
5.3.12 OTHER APPLICATIONS OF NMR SPECTROSCOPY TO
SOLID-PHASE SYNTHESIS 227 5.4 IR TECHNIQUES FOR SOLID-PHASE SYNTHESIS
228 5.4.1 EXAMPLES OF SOLID-PHASE INFRARED SPECTROSCOPY WITH STANDARD
KBR PELLETS 228
5.4.2 INFRARED SPECTRUM OF A SINGLE RESIN BEAD FOR REAL-TIME MONITORING
OF SOLID-PHASE REACTIONS 230 5.4.3 PROGRESSION OF ORGANIC REACTIONS ON
SOLID SUPPORTS MONITORED BY SINGLE-BEAD FT-IR MICROSPECTROSCOPY 231
5.4.4 OTHER APPLICATIONS OFIR SPECTROSCOPY TO
SOLID-PHASE SYNTHESIS 232 5.5 MASS SPECTROMETRY TECHNIQUES FOR
SOLID-PHASE SYNTHESIS 233 5.5.1 THE APPLICATION OF SOLID-PHASE IN SITU
MASS SPECTROMETRY
FOR REACTION ANALYSIS WITH A RANGE OF TRADITIONAL PEPTIDE LINKERS 233
5.5.2 DIRECT MONITORING BY MALDI-TOF MS: A TOOL FOR COMBINATORIAL
CHEMISTRY 234 5.6 OTHER ANALYTICAL METHODS FOR COMBINATORIAL SYNTHESIS
235
5.6.1 QUANTITATION OF COMBINATORIAL LIBRARIES OF SMALL ORGANIC MOLECULES
BY NORMAL-PHASE HPLC WITH EVAPORATIVE LIGHT-SCATTERING DETECTION 235
6 PREPARATION OF SOLUTION LIBRARIES AND COMBINED APPROACHES AT THE
SOLUTION/SOLID-PHASE INTERFACE 237
6.1 SOLUTION LIBRARIES 240 6.1.1 SYNTHESIS AND SCREENING PROCEDURES FOR
SOLUTION LIBRARIES ON TETRASUBSTITUTED TEMPLATES 240 6.1.2 A NOVEL
SOLUTION-PHASE STRATEGY FOR THE SYNTHESIS OF TRIAMIDE
LIBRARIES CONTAINING SMALL ORGANIC MOLECULES 241
IMAGE 10
CONTENTS XIII
6.1.3 SOLUTION SYNTHESIS AND BIOLOGICAL EVALUATION OF A LIBRARY
CONTAINING POTENTIALLY 1600 AMIDES/ESTERS 243 6. 1.4 AUTOMATED PARALLEL
SOLUTION-PHASE SYNTHESIS AND PURIFICATION OF AMIDES 245 6.1.5 SOLUTION
AND SOLID-PHASE SYNTHESIS OF 5-ALKOXYHYDANTOINS 246
6.1.6 LIQUID-PHASE COMBINATORIAL SYNTHESIS ON POLYFETHYLENE
GLYCOL)MONOMETHYL ETHER (MEO-PEG) 247 6.1.7 A FLUOROUS TIN HYDRIDE
REAGENT FOR LIQUID-PHASE COMBINATORIAL SYNTHESIS 249 6.1.8 STILLE
COUPLINGS WITH FLUOROUS TIN REACTANTS FOR LIQUID-PHASE
COMBINATORIAL SYNTHESIS 249 6.1.9 SOLUTION-PHASE COMBINATORIAL SYNTHESIS
OF POLYAZACYCLOPHANE SCAFFOLDS AND TERTIARY AMINE LIBRARIES 250 6.1.10
PARALLEL-COMPOUND SOLUTION-PHASE SYNTHESIS FOR
LEAD OPTIMIZATION 251 6.1.11 ROBOTIC AND SOLUTION-PHASE DERIVATIZATION
OF DICBLOROTRIAZINES 254 6.1.12 MULTIPLE-COMPONENT CONDENSATION
STRATEGIES IN SOLUTION-PHASE
COMBINATORIAL SYNTHESIS 255 6.1.13 POSTCONDENSATION MODIFICATIONS OF UGI
FOUR-COMPONENT CONDENSATION PRODUCTS 257 6.2 RESIN CAPTURE 259
6.2.1 SOLID-PHASE, PARALLEL SYNTHESIS BY THE UGI MULTICOMPONENT
CONDENSATION 259 6.2.2 SYNTHESIS OFTETRASUBSTITUTED ETHYLENES ON SOLID
SUPPORT VIA RESIN CAPTURE 260 6.3 SUPPORT-BOUND REAGENTS 262
6.3.1 SUPPORT-BOUND ACTIVATED NITROPHENYL ESTERS 262 6.3.2 MEDIATOR
METHODOLOGY: A TWO-POLYMERIC SYSTEM 264 633 POLYMER-BOUND EDCI: A
CONVENIENT REAGENT FOR FORMATION OF AN AMIDE BOND 266
6.3.4 A HIGHLY REACTIVE ACYLSULFONAMIDE LINKER 267 63.5 USE OF
ANION-EXCHANGE RESINS FOR THE SOLUTION-PHASE SYNTHESIS OF COMBINATORIAL
LIBRARIES CONTAINING ARYL AND HETEROARYL ETHERS 269
6.3.6 SIMULTANEOUS MULTISTEP SYNTHESIS USING POLYMERIC REAGENTS 270 63.7
POLYMER-SUPPORTED PHOSPHONATES: OLEFINS FROM ALDEHYDES, KETONES, AND
DIOXOLANES 271 6.3.8 ONE-POT SOLUTION-PHASE CLEAVAGE OFA-DIOLS TO
PRIMARY ALCOHOLS
WITH POLYMER-SUPPORTED ANTAGONISTIC REAGENTS: PERIODATE AND BOROHYDRIDE
2 72 6.3.9 INVESTIGATIONS ON THE STILLE REACTION WITH POLYMER-SUPPORTED
ORGANOTIN REAGENTS 273 6.3.10 AN IMPROVED PROTOCOL FOR SOLUTION-PHASE
AZOLE SYNTHESIS WITH
PEG-SUPPORTED BURGESS REAGENT 274 6.3.11 SUPPORT-BOUND NUCLEOPHILES AND
EIECTROPHILES FOR THE PURIFICATION OF SMALL-MOLECULE LIBRARIES 275
IMAGE 11
CONTENTS
6.3.12 A POLYMER-SUPPORTED SCANDIUM CATALYST FOR SOLUTION- PHASE
SYNTHESIS 277 6.3.13 POLYMER SCANDIUM-CATALYZED 3 CC LEADING TO DIVERSE
AMINO KETONE, AMINO ESTER, AND AMINO NITRILE DERIVATIVES 278 6.3.14 A
NEW METHODOLOGY FOR SOLUTION-PHASE COMBINATORIAL
SYNTHESIS: CONSTRUCTION OF A QUINOLINE LIBRARY USING A POLYMER-
SUPPORTED CATALYST 279 6.3.15 ADDITIONAL EXAMPLES OF SUPPORT-BOUND
CATALYSTS 280
APPENDIX I SUMMARY OF FUNCTIONAL GROUP TRANSFORMATIONS FOR COMBINATORIAL
SOLID-PHASE SYNTHESIS 281
APPENDIX 2 CLASSIFICATION OF HETEROCYCLIZATION REACTIONS 295
APPENDIX 3 UNNATURAL BIOPOLYMERS 303
APPENDIX 4 OLIGOSACCHARIDES 305
APPENDIX 5 LIST OF ABBREVIATIONS 307
AUTHOR INDEX 309 SUBJECT INDEX 319
|
| any_adam_object | 1 |
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| building | Verbundindex |
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| callnumber-first | R - Medicine |
| callnumber-label | RS419 |
| callnumber-raw | RS419 |
| callnumber-search | RS419 |
| callnumber-sort | RS 3419 |
| callnumber-subject | RS - Pharmacy |
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| ctrlnum | (OCoLC)38847491 (DE-599)BVBBV013268724 |
| dewey-full | 615/.19 |
| dewey-hundreds | 600 - Technology (Applied sciences) |
| dewey-ones | 615 - Pharmacology and therapeutics |
| dewey-raw | 615/.19 |
| dewey-search | 615/.19 |
| dewey-sort | 3615 219 |
| dewey-tens | 610 - Medicine and health |
| discipline | Chemie / Pharmazie Medizin |
| format | Book |
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Bunin</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">San Diego [u.a.]</subfield><subfield code="b">Acad. Press</subfield><subfield code="c">1998</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">XVII, 322 S.</subfield><subfield code="b">Ill.</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1="1" ind2=" "><subfield code="a">"Combinatorial chemistry has become a major focus of research activity for pharmaceutical, agrochemical, and biotechnology companies. The explosion of combinatorial methods has created the need for a compendium of reliable synthetic transformations from the primary literature. The Combinatorial Index fills this need. Included are chapters on linkers, solid-phase synthetic methods, analytical techniques, and solution libraries. Procedures from the literature for constructing combinatorial libraries of small molecules comprise an indispensable laboratory reference for the synthetic chemist. Each procedure in the compilation is preceded by a section entitled "Points of Interest," which highlights the strengths and limitations of the various methods. A structural appendix covers both functional group transformations and heterocyclization reactions in solid-phase synthesis. This comprehensive but easy-to-access guide to the combinatorial chemistry literature will save time on tedious library searches, introduce a growing audience of chemists to this exciting field, and lower the barriers to attempting a new or related methodology."--BOOK JACKET.</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Chimie combinatoire</subfield><subfield code="2">ram</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Combinatorische chemie</subfield><subfield code="2">gtt</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Composés organiques - Synthèse</subfield><subfield code="2">ram</subfield></datafield><datafield tag="650" ind1=" " ind2="7"><subfield code="a">Peptiden</subfield><subfield code="2">gtt</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Combinatorial chemistry</subfield><subfield code="v">Handbooks, manuals, etc</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Molekülbibliothek</subfield><subfield code="0">(DE-588)4420227-1</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Molekülbibliothek</subfield><subfield code="0">(DE-588)4420227-1</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">GBV Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009046278&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-009046278</subfield></datafield></record></collection> |
| id | DE-604.BV013268724 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T18:42:50Z |
| institution | BVB |
| isbn | 0121413403 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009046278 |
| oclc_num | 38847491 |
| open_access_boolean | |
| owner | DE-703 |
| owner_facet | DE-703 |
| physical | XVII, 322 S. Ill. |
| publishDate | 1998 |
| publishDateSearch | 1998 |
| publishDateSort | 1998 |
| publisher | Acad. Press |
| record_format | marc |
| spelling | Bunin, Barry A. Verfasser aut The combinatorial index Barry A. Bunin San Diego [u.a.] Acad. Press 1998 XVII, 322 S. Ill. txt rdacontent n rdamedia nc rdacarrier "Combinatorial chemistry has become a major focus of research activity for pharmaceutical, agrochemical, and biotechnology companies. The explosion of combinatorial methods has created the need for a compendium of reliable synthetic transformations from the primary literature. The Combinatorial Index fills this need. Included are chapters on linkers, solid-phase synthetic methods, analytical techniques, and solution libraries. Procedures from the literature for constructing combinatorial libraries of small molecules comprise an indispensable laboratory reference for the synthetic chemist. Each procedure in the compilation is preceded by a section entitled "Points of Interest," which highlights the strengths and limitations of the various methods. A structural appendix covers both functional group transformations and heterocyclization reactions in solid-phase synthesis. This comprehensive but easy-to-access guide to the combinatorial chemistry literature will save time on tedious library searches, introduce a growing audience of chemists to this exciting field, and lower the barriers to attempting a new or related methodology."--BOOK JACKET. Chimie combinatoire ram Combinatorische chemie gtt Composés organiques - Synthèse ram Peptiden gtt Combinatorial chemistry Handbooks, manuals, etc Molekülbibliothek (DE-588)4420227-1 gnd rswk-swf Molekülbibliothek (DE-588)4420227-1 s DE-604 GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009046278&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bunin, Barry A. The combinatorial index Chimie combinatoire ram Combinatorische chemie gtt Composés organiques - Synthèse ram Peptiden gtt Combinatorial chemistry Handbooks, manuals, etc Molekülbibliothek (DE-588)4420227-1 gnd |
| subject_GND | (DE-588)4420227-1 |
| title | The combinatorial index |
| title_auth | The combinatorial index |
| title_exact_search | The combinatorial index |
| title_full | The combinatorial index Barry A. Bunin |
| title_fullStr | The combinatorial index Barry A. Bunin |
| title_full_unstemmed | The combinatorial index Barry A. Bunin |
| title_short | The combinatorial index |
| title_sort | the combinatorial index |
| topic | Chimie combinatoire ram Combinatorische chemie gtt Composés organiques - Synthèse ram Peptiden gtt Combinatorial chemistry Handbooks, manuals, etc Molekülbibliothek (DE-588)4420227-1 gnd |
| topic_facet | Chimie combinatoire Combinatorische chemie Composés organiques - Synthèse Peptiden Combinatorial chemistry Handbooks, manuals, etc Molekülbibliothek |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009046278&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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