Solid-Phase Organic Synthesis

Name: Solid-Phase Organic Synthesis | Concepts, Strategies, and Applications
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Concepts, Strategies, and Applications

Patrick H. Toy Yulin Lam(Herausgeber*in)

Wiley (Verlag)

Erschienen am 27. Dezember 2011

560 Seiten

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Presents both the fundamental concepts and the most recent applications in solid-phase organic synthesis
With its emphasis on basic concepts, Solid-Phase Organic Synthesis guides readers through all the steps needed to design and perform successful solid-phase organic syntheses. The authors focus on the fundamentals of heterogeneous supports in the synthesis of organic molecules, explaining the use of a solid material to facilitate organic synthesis. This comprehensive text not only presents the fundamentals, but also reviews the most recent research findings and applications, offering readers everything needed to conduct their own state-of-the-art science experiments.
Featuring chapters written by leading researchers in the field, Solid-Phase Organic Synthesis is divided into two parts:
* Part One, Concepts and Strategies, discusses the linker groups used to attach the synthesis substrate to the solid support, colorimetric tests to identify the presence of functional groups, combinatorial synthesis, and diversity-oriented synthesis. Readers will discover how solid-phase synthesis is currently used to facilitate the discovery of new molecular functionality. The final chapter discusses how using a support can change or increase reaction selectivity.
* Part Two, Applications, presents examples of the solid-phase synthesis of various classes of organic molecules. Chapters explore general asymmetric synthesis on a support, strategies for heterocyclic synthesis, and synthesis of radioactive organic molecules, dyes, dendrimers, and oligosaccharides.
Each chapter ends with a set of conclusions that underscore the key concepts and methods. References in each chapter enable readers to investigate any topic in greater depth.
With its presentation of basic concepts as well as recent findings and applications, Solid-Phase Organic Synthesis is the ideal starting point for students and researchers in organic, medicinal, and combinatorial chemistry who want to take full advantage of current solid-phase synthesis techniques.

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SOLID-PHASE ORGANIC SYNTHESIS: Concepts, Strategies, and Applications
CONTENTS
Preface
Acknowledgments
Contributors
Part I: CONCEPTS AND STRATEGIES
1 LINKER STRATEGIES IN MODERN SOLID-PHASE ORGANIC SYNTHESIS
1.1 Introduction
1.2 Classical Linker Strategies
1.2.1 Acid and Base Cleavable Linker Units
1.2.2 Cyclorelease Linker Units
1.2.3 Traceless Linker Units
1.2.4 Photolabile Linker Units
1.2.5 Safety-Catch Linker Units
1.3 Multifunctional Linker Strategies
1.3.1 Nitrogen Linker Units
1.3.1.1 Triazene Linker Units
1.3.1.2 Hydrazone Linker Units
1.3.1.3 Benzotriazole Linker Units
1.3.2 Sulfur Linker Units
1.3.3 Phosphorus Linker Units
1.3.4 Selenium and Tellurium Linker Units
1.3.5 Silyl and Germyl Linker Units
1.3.6 Boron and Stannane Linker Units
1.3.7 Bismuth Linker Units
1.3.8 Alkene Linker Units
1.4 Conclusions
References
2 COLORIMETRIC TEST FOR SOLID-PHASE ORGANIC SYNTHESIS
2.1 Introduction
2.2 Functional Group Tests
2.2.1 Amine Groups
2.2.1.1 Ninhydrin (Kaiser) Test
2.2.1.2 TNBSA Test
2.2.1.3 Bromophenol Blue Test
2.2.1.4 Chloranil Test
2.2.1.5 DABITC Test
2.2.1.6 MGI Test
2.2.1.7 Isatin Test
2.2.1.8 DESC Test
2.2.1.9 NPIT Test
2.2.1.10 NF31 Test
2.2.1.11 Nondestructive NF31 Test
2.2.1.12 Naphthol Test
2.2.1.13 2-Amino-3-chloro-1,4-naphthoquinone Test
2.2.2 Alcohols
2.2.2.1 PNBP Test
2.2.2.2 TCT-AliR and TCT-Fluorescein Test
2.2.2.3 Diphenyldichlorosilane-Methyl Red Test
2.2.2.4 9-Anthronylnitrile Test
2.2.2.5 NMA Test
2.2.2.6 Protecting Group NPB Test
2.2.2.7 Methyl Red/DIC Test
2.2.2.8 Other Methods
2.2.3 Thiol Groups
2.2.3.1 Ellman's Test
2.2.3.2 Other Methods
2.2.4 Halogen Groups
2.2.4.1 Fluorescein Test
2.2.4.2 Other Methods
2.2.5 Carboxylic Acid Groups
2.2.5.1 Malachite Green Test
2.2.5.2 PDAM Test
2.2.6 Aldehyde and Ketone Groups
2.2.6.1 Fluorescent Dansylhydrazine Test
2.2.6.2 p-Anisaldehyde Test
2.2.6.3 Purpald Test
2.3 Conclusions
References
3 PRACTICAL ASPECTS OF COMBINATORIAL SOLID-PHASE SYNTHESIS
3.1 Introduction
3.1.1 What Is Combinatorial Chemistry
3.1.2 What Is Not Combinatorial Chemistry
3.1.3 History of Combinatorial Chemistry: Breakthrough Discoveries That Shaped the Future of the Combinatorial Chemistry Field
3.1.3.1 Solid-Phase Synthesis
3.1.3.2 Pooling Strategy
3.1.3.3 Parallel Synthesis
3.2 Strategies in Combinatorial Solid-Phase Synthesis
3.2.1 Random Split-and-Pool Method
3.2.1.1 One-Bead-One-Compound Concept
3.2.1.2 Encoding Methods for the OBOC Technique
3.2.1.3 Organized Mixtures
3.2.2 Directed Split-and-Pool Method in Practice
3.2.2.1 Formulation of Solid-Phase Supports for the Directed Split-and-Pool Technique
3.2.2.2 Chemical History of the Resin Formulations
3.3 Equipment and Instrumentation
3.3.1 Manual Solid-Phase Synthesis
3.3.2 Integrated Semiautomated Synthesis
3.3.3 Fully Automated Synthesizers (Gone with the Wind)
3.3.4 Instruments for Sorting
3.4 Characterization and Purification
3.5 Conclusions
Acknowledgments
References
4 DIVERSITY-ORIENTED SYNTHESIS
4.1 Introduction
4.2 Small Molecules and Biology
4.3 Diversity-Oriented Synthesis, Target-Oriented Synthesis, and Combinatorial Chemistry
4.4 Molecular Diversity
4.4.1 Molecular Diversity and Chemical Space
4.4.2 Synthetic Strategies for Creating Molecular Diversity
4.5 Diversity-Oriented Synthesis on Solid Phase
4.5.1 Reagent-Based Strategies
4.5.2 Substrate-Based Strategies
4.5.3 Build/Couple/Pair Strategies
4.6 Diversity-Oriented Synthesis Around Privileged Scaffolds
4.7 Diversity Linker Units in Solid-Phase Organic Synthesis
4.8 Conclusions
References
5 DIVERSITY-ORIENTED SYNTHESIS OF PRIVILEGED HETEROCYCLES USING DIVERGENT STRATEGY
5.1 Introduction
5.2 Divergent Synthesis of Natural Product-Like Polyheterocycles Using a Cyclic Iminium as a Single Key Intermediate
5.2.1 Practical Solid-Phase Synthesis of Diaza-briged Heterocycle and Tetrahydro-beta-carboline Through Intramolecular Pictet-Spengler Cyclization (Type I, II, and III)
5.2.1.1 Synthesis of Diaza-Bridged Heterocycles (Type I and II)
5.2.1.2 Synthesis of Tetrahydro-beta-carbolines (Type III)
5.2.2 Practical Solid-Phase Synthesis of ?5-2-Oxopiperazines via N-Acyliminium Ion Cyclization (Type IV)
5.2.3 Novel Application of the Leuckart-Wallach Reaction for the Synthesis of a Tetrahydro-1,4-benzodiazepin-5-one Library (Type V)
5.3 Conclusions
References
6 CHEMO- AND REGIOSELECTIVITY ENHANCEMENT IN SOLID-SUPPORTED REACTIONS
6.1 Introduction
6.2 Transition Metal-Mediated Solid-Supported Reactions
6.2.1 Olefin Metathesis Reactions
6.2.1.1 Olefin Cross Metathesis
6.2.1.2 Ring-Closing Metathesis
6.2.1.3 Ring-Opening Metathesis
6.2.2 [2 + 2 + 2] Cyclotrimerization Reactions
6.2.3 Pauson-Khand Reactions
6.2.4 Miscellaneous Transition Metal-Mediated Reactions
6.2.4.1 Dötz Benzannulation Reactions
6.2.4.2 Cadiot-Chodkiewicz Coupling Reactions
6.2.4.3 Cyclopropanation Reactions
6.2.4.4 Heck Reactions
6.3 Non-transition Metal-Mediated Solid-Supported Reactions
6.3.1 Cycloaddition Reactions
6.3.2 Hydroxylation Reactions
6.3.3 Aldol Condensation Reactions
6.3.4 Radical Reactions
6.3.5 Oxidative Coupling Reactions
6.4 Traceless Cleavage
6.4.1 Cyclizative Cleavage
6.4.2 Cyclizative Immobilization
6.4.3 Chemoselective Cleavage
6.5 Conclusions
References
Part II: Applications
7 ASYMMETRIC SYNTHESIS ON SOLID SUPPORT
7.1 Introduction
7.2 Asymmetric Chemical Transformations of Solid-Supported Substrates
7.2.1 Asymmetric Aldol Reactions
7.2.2 Asymmetric Allylation Reactions
7.2.3 Enantioselective Cycloaddition Reactions
7.2.4 Stereoselective Epoxide Ring-Opening Reactions
7.2.5 Asymmetric Alkene Cyclopropanation Reactions
7.2.6 Enantioselective Alkylation Reactions
7.3 Asymmetric Transformations Using Resin-Bound Chiral Catalysts and Auxiliaries
7.3.1 Catalytic Asymmetric Synthesis with Resin-Bound Chiral Catalysts
7.3.2 Asymmetric Synthesis Using Resin-Bound Chiral Auxiliaries
7.4 Conclusions
References
8 RECENT ADVANCES IN MICROWAVE-ASSISTED SOLID-PHASE SYNTHESIS OF HETEROCYCLES
8.1 Introduction
8.2 Fused 1,3-oxazin-6-ones
8.3 Thiazolo[4,5-d]pyrimidine-5,7-diones
8.4 Pyrazoles
8.5 HSP70 Modulators
8.6 Benzimidazo[2,1-b]quinazolin-12(5H)-ones
8.7 Imidazoles
8.8 1,4-Naphthoquinones
8.9 Phthalocyanines
8.10 1,2,3,4-Tetrahydroquinolines
8.11 1,2,3-Triazoles
8.12 2,8-Diaminopurines
8.13 Imidazolidin-4-ones
8.14 Indoles
8.15 1,2,3,4-Tetrahydroquinolines Using a SmI2-Cleavable Linker
8.16 Hydantoins
8.17 Imatinib
8.18 Isoindolines
8.19 2-(Benzylthio)imidazo[1,2a]-pyrimidin-5-ones
8.20 2-Aminobenzothiazoles
8.21 Pyrimidines, Pyrazoles, and Isoxazoles
8.22 Quinolin-2(1H)-ones and Coumarins
8.23 Benzofurans
8.24 i-Condensed Purines
8.25 2(1H)-Pyrazinones
8.26 Conclusions
References
9 SOLID-PHASE SYNTHESIS OF HETEROCYCLES FROM PEPTIDES AND AMINO ACIDS
9.1 Introduction
9.2 Synthesis of Various Heterocycles
9.2.1 Three-Membered Ring Heterocycles
9.2.2 Four-Membered Ring Heterocycles
9.2.3 Synthesis of Five-Membered Ring Heterocycles
9.2.3.1 Five-Membered Ring Heterocycles Containing One Nitrogen Atom
9.2.3.2 Five-Membered Ring Heterocycles Containing Two Nitrogen Atoms
9.2.3.3 Five-Membered Ring Heterocycles Containing Three Nitrogen Atoms
9.2.3.4 Five-Membered Ring Heterocycles Containing Four Nitrogen Atoms
9.2.4 Six-Membered Ring Heterocycles
9.2.4.1 Six-Membered Ring Heterocycles Containing One Nitrogen Atom
9.2.4.2 Six-Membered Ring Heterocycles Containing Two or More Nitrogen Atoms
9.2.5 Seven-Membered Ring Heterocycles
References
10 GENERATION OF DRUG-LIKE FIVE-MEMBERED HETEROCYCLIC LIBRARIES USING CARBON DISULFIDE AND MERRIFIELD RESIN
10.1 Introduction
10.2 Solid-Phase Synthesis of Related Thiazole Compounds
10.2.1 Solid-Phase Synthesis of 2,4,5-Trisubstituted Thiazoles
10.2.2 Solid-Phase Synthesis of 2,5,6,7-Tetrasubstituted Thiazolo[4,5-b]pyridines
10.2.3 Solid-Phase Synthesis of 2,4,6-Trisubstituted Thiazolo[4,5-d]pyrimidine-5,7-diones
10.2.4 Solid-Phase Synthesis of 1,3,6-Trisubstituted 1H-Thiazolo[4,5-c][1,2]thiazin-4(3H)one-2,2-dioxides
10.3 Solid-Phase Synthesis of Benzoxazoles
10.4 Solid-Phase Synthesis of Related Pyrazole Compounds and 1,3,4-Triazoles via a Dithiocarbazate Linker
10.4.1 Synthesis of a Dithiocarbazate Linker on Solid Support
10.4.2 Solid-Phase Synthesis of Pyrazoles via a Dithiocarbazate Linker
10.4.3 Solid-Phase Synthesis of Pyrazolo[1,5-a][1,3,5]-2-oxo-4- dithioxotriazines
10.4.4 Solid-Phase Synthesis of Pyrazolo[1,5-a][1,3,5]-2,4- dithioxotriazines
10.4.5 Solid-Phase Synthesis of 1,3,4-Triazoles
10.5 Solid-Phase Synthesis of 1,3,4-Oxadiazoles and 1,3,4-Thiadiazoles via Selective Cyclization
10.6 Solid-Phase Synthesis of 1,2,4-Thiadiazoles
10.7 Summary
References
11 RECENT ADVANCES IN SOLID-PHASE 1,3-DIPOLAR CYCLOADDITION REACTIONS
11.1 Introduction
11.2 Solid-Phase Synthesis of Pyrrolidines, Pyrrolines, and Pyrroles
11.3 Synthesis of Pyrazolines and Pyrazoles
11.4 Solid-Phase Synthesis of Imidazoles, 1,2,4-Triazoles, and 1,2,3-Triazoles
11.5 Solid-Phase Synthesis of Isoxazolidines, Isoxazolines, and Isoxazoles
11.6 Conclusions
References
12 SULFONES IN SOLID-PHASE HETEROCYCLE SYNTHESIS
12.1 Introduction
12.2 Linkers
12.2.1 Sulfone Chemistry
12.2.2 Sulfone Linker Units
12.2.2.1 Preparation of Sulfone Linkers
12.2.2.2 Cleavage of Sulfone Linkers
12.2.2.3 Sulfone Linkers in Oligosaccharide Synthesis
12.3 Conclusions
References
13 SOLID-PHASE ORGANIC RADIOSYNTHESIS
13.1 Introduction
13.2 Solid-Phase Organic Radiosynthesis with Fluorine-18
13.2.1 Radiolabeled Peptides with Fluorine-18
13.2.2 Solid-Phase Organic Radiosynthesis of [18F]FDG
13.2.3 Fluorine-18 Displacement of Supported Aryliodonium
13.2.4 Solid-Phase Organic Radiosynthesis of 18FCH2Br
13.2.5 Solid-Phase Organic Radiosynthesis of [18F]FluoroDOPA
13.2.6 Solid-Phase Organic Radiosynthesis of b-Amyloid PET Tracers
13.2.7 Solid-Phase Organic Radiosynthesis of Oncological PET Tracers
13.3 Solid-Phase Organic Radiosynthesis with Carbon-11
13.4 Solid-Phase Organic Radiosynthesis with Other Radioisotopes
13.4.1 Solid-Phase Purification of Copper-64 Metalloradiopharmaceuticals
13.4.2 Solid-Phase Radiosynthesis of [131I]MIBG
13.5 Conclusions
References
14 SOLID-PHASE SYNTHESIS OF DYES AND THEIR APPLICATION AS SENSORS AND BIOIMAGING PROBES
14.1 Introduction
14.2 On-Bead Sensors
14.3 Solid-Phase Approaches in Fluorescent Labeling
14.4 Solid-Phase Derivatization of Fluorescent Scaffolds
14.5 Diversity-Oriented Fluorescent Libraries
14.6 Conclusions
14.7 Acknowledgments
References
15 DENDRITIC MOLECULES ON SOLID SUPPORT: SOLID-PHASE SYNTHESIS AND APPLICATIONS
15.1 Introduction
15.2 Synthesis
15.2.1 General Synthetic Schemes
15.2.2 Preparation of Polyamide Dendrons
15.2.2.1 Polylysine Dendrons
15.2.2.2 Dendrons Combining Natural and Artificial Amino Acids
15.2.2.3 Dendrons Made of Artificial Amino Acids
15.2.2.4 Polyamide Dendrons from Alternative Building Blocks
15.2.3 Preparation of Polyamidoamine Dendrons
15.2.4 Preparation of Polyurea Dendrons
15.2.5 Preparation of Polyester Dendrons
15.2.6 Preparation of Polyether Dendrons
15.2.7 Preparation of Polythioether Dendrons
15.2.8 Preparation of Polyamine Dendrons
15.2.9 Preparation of Dendrons Based on 1,3,5-Triazines
15.2.10 Preparation of Poly(arylacetylene) Dendrons
15.2.11 Coordination-Linked Dendrons
15.3 Applications of Dendronized Supports
15.3.1 Dendronized Supports as Synthetic Intermediates
15.3.2 High-Loading Dendronized Supports for Solid-Phase Synthesis
15.3.3 Dendronized Supports for Multivalent Molecular Recognition
15.3.4 Supported Dendritic Catalysts
15.3.5 Dendronized Supports in Separation Processes
15.3.6 Dendronized Surfaces for Immobilization of Biomacromolecules
15.3.7 Other Applications
15.4 Conclusions
References
16 OLIGOSACCHARIDE SYNTHESIS ON SOLID, SOLUBLE POLYMER, AND TAG SUPPORTS
16.1 Introduction
16.2 Solid-Phase Methods for Synthesis of Oligosaccharides
16.2.1 New Linkers and Protection Groups for Solid-Phase Synthesis of Oligosaccharides
16.2.2 Application of Unique Glycosylation Methods in Solution to Solid-Phase Synthesis of Oligosaccharides
16.2.3 Solid-Phase Synthesis of Complex Oligosaccharides
16.2.4 Solid-Phase Methods for Purification of Synthesized Oligosaccharides
16.2.5 Monitoring of Solid-Phase Reactions
16.3 Polymer-Supported and Tag-Assisted Oligosaccharide Synthesis in Solution
16.3.1 Polymer-Supported Synthesis of Oligosaccharides
16.3.2 Tag-Assisted Synthesis of Oligosaccharides
16.3.3 Polymer-Supported Enzymatic Synthesis of Oligosaccharides
16.3.4 Microfluidic Methods for Oligosaccharide Synthesis
16.4 Conclusions
16.5 Acknowledgments
References
Index
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