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Preparation of Compounds Labeled with Tritium and Carbon-14

Preparation of Compounds Labeled with Tritium and Carbon-14

Rolf Voges, J. Richard Heys, Thomas Moenius

ISBN: 978-0-470-74344-7

Mar 2009

682 pages

Description

Compounds labeled with carbon-14 and tritium are indispensable tools for research in biomedical sciences, discovery and development of pharmaceuticals and agrochemicals.

Preparation of Compounds Labeled with Tritium and Carbon-14 is a comprehensive, authoritative and up-to-date discussion of the strategies, synthetic approaches, reactions techniques, and resources for the preparation of compounds labeled with either of these isotopes. A large number of examples are presented for the use of isotopic sources and building blocks in the preparation of labeled target compounds, illustrating the range of possibilities for embedding isotopic labels in selected moieties of complex structures.  Topics include:

  •  Formulation of synthetic strategies for preparing labeled compounds
  • Isotope exchange methods and synthetic alternatives for preparing tritiated compounds
  • In-depth discussion of carbon-14 building blocks and their utility in synthesis
  • Preparation of enantiomerically pure isotopically labeled compounds
  • Applications of biotransformations

Preparation of Compounds Labeled with Tritium and Carbon-14 is an essential guide to the specialist strategies and tactics used by chemists to prepare compounds tagged with theradioactive atoms carbon-14 and tritium.

Preface.

Glossary.

Author Biographies.

1 Introduction.

1.1 Physical Properties of Tritium and Carbon-14.

1.2 Purification.

1.3 Analysis.

1.4 Stability and Storage of Compounds Labeled with Tritium or Carbon-14.

1.5 Specialist Techniques and Equipment.

References .

2 Strategies for Target Preparation.

2.1 Formulating Target Specifications.

2.2 Planning Radiotracer Preparations.

References.

3 Preparation of Tritium-Labeled Compounds by Isotope Exchange Reactions.

3.1 Homogeneous Acid- or Base-Catalyzed Exchange.

3.2 Heterogeneous Catalysis with Tritium in Solvent.

3.3 Heterogeneous Catalysis in Solution with Tritium Gas.

3.4 Homogeneous Catalysis in Solution with Tritiated Water.

3.5 Homogeneous Catalysis with Tritium Gas.

3.6 Solvent-Free Catalytic Exchange.

References.

4 Preparation of Tritium-Labeled Compounds by Chemical Synthesis.

4.1 Catalytic Tritiations.

4.2 Catalytic Tritiolyses.

4.3 Tritide Reductions.

4.4 Small Tritiated Building Blocks.

References.

5 Barium [14C]Carbonate and the Preparation of Carbon-14-Labeled Compounds via One-Carbon Building Blocks of the [14C]Carbon Dioxide Tree.

5.1 [14C]Carbon Dioxide (14CO2).

5.2 [14C]Carbon Monoxide (14CO).

5.3 [14C]Formic Acid (H14COOH).

5.4 [14C]Formaldehyde (H14CHO).

5.5 [14C]Methyl Iodide (14CH3I).

5.6 [14C]Nitromethane (14CH3NO2).

References.

6 Preparation of Carbon-14-Labeled Compounds via Multi-Carbon Building Blocks of the [14C]Carbon Dioxide Tree.

6.1 [14C]Acetic Acid and Its Derivatives.

6.2 Halo[14C]acetates.

6.3 [14C]Acetone.

6.4 Alkyl [14C]Acetoacetate.

6.5 [14C]Malonates.

References.

7 Preparation of Carbon-14-Labeled Compounds via the [14C]Cyanide Tree.

7.1 Metal [14C]Cyanides.

7.2 Preparation of Other Building Blocks from [14C]Cyanide.

References.

8 Preparation of Carbon-14-Labeled Compounds via the [14C2]Acetylene Tree.

8.1 [14C2]Acetylene (H14C≡14CH).

8.2 [14C2]Acetaldehyde (14CH3 14CHO).

8.3 [1,2-14C2]Acetic Acid (14CH3 14COOH).

8.4 2-[2,3-14C2]Propyne-1-ol ([2,3-14C2]Propargyl Alcohol) and 2-[2,3-14C2]Butyne-1,4-diol.

8.5 Methyl [2,3-14C2]Propiolate (H14C≡14CCOOMe) and Dimethyl [2,3-14C2]Acetylenedicarboxylate (HOOC14C_14CCOOH).

8.6 1,2-[14C2]Dibromoethane (Br14CH2 14CH2Br).

8.7 [14C2]Ethylene Oxide.

8.8 [14Cn]Benzene and the Synthesis of Ring-Labeled Aromatic Compounds.

References.

9 Preparation of Carbon-14-Labeled Compounds via the [14C]Cyanamide Tree.

9.1 [14C]Cyanamide (H2N14C≡N).

9.2 [14C]Guanidine (H2N14C=NH)NH2).

9.3 [14C]Urea, H2N14CONH2.

9.4 [14C]Thiourea, H2N14CSNH2 .

References.

10 Reconstitution Strategies.

10.1 Replacement Strategies.

10.2 Disconnection?Reconnection Strategies.

References.

11 Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon.

11.1 Resolution of Racemates.

11.2 Enantioselective Synthetic Methods.

11.3 Diastereoselective Synthetic Procedures.

References.

12 Biotransformations in the Preparation of Compounds Labeled with Carbon and Hydrogen Isotopes.

12.1 Applications of Isolated Enzymes.

12.2 Application of Cell-Containing Systems.

12.3 Biocatalyzed Synthesis of Key Intermediates for Reconstitution Approaches.

References.

Index.