Protecting groups /

Protecting groups /

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Bibliographic Details
Author / Creator:Kocienski, Philip J.
Edition:3rd ed.
Imprint:Stuttgart ; New York : Georg Thieme, c2004.
Description:xvi, 679 p. : ill. (some col.) ; 25 cm.
Language:English
Subject:
Organic compounds -- Synthesis.
Protective groups (Chemistry)
Organic compounds -- Synthesis.
Protective groups (Chemistry)
Format: Print Book
URL for this record:http://pi.lib.uchicago.edu/1001/cat/bib/5274505
Hidden Bibliographic Details
ISBN:1588902358 (TNY, New York)
3131370033 (GTV, Stuttgart)
Notes:Includes bibliographical references and index.
Table of Contents:
  • Chapter 1. Protecting Groups: An Overview
  • 1.1. Death, Taxes, and Protecting Groups
  • 1.2. Deprotection: The Concept of Orthogonal Sets
  • 1.2.1. Protecting Groups Cleaved by Basic Solvolysis
  • 1.2.2. Protecting Groups Cleaved by Acid
  • 1.2.3. Protecting Groups Cleaved by Heavy Metals
  • 1.2.4. Protecting Groups Cleaved by Fluoride Ions
  • 1.2.5. Protecting Groups Cleaved by Reductive Elimination
  • 1.2.6. Protecting Groups Cleaved by [beta]-Elimination Reactions
  • 1.2.7. Protecting Groups Cleaved by Hydrogenolysis
  • 1.2.8. Protecting Groups Cleaved by Oxidation
  • 1.2.9. Protecting Groups Cleaved by Dissolving Metal Reduction
  • 1.2.10. Protecting Groups Cleaved by Nucleophilic Substitution
  • 1.2.11. Protecting Groups Cleaved by Transition Metal Catalysis
  • 1.2.12. Protecting Groups Cleaved by Light
  • 1.2.13. Protecting Groups Cleaved by Enzymes
  • 1.3. Relay Deprotection
  • 1.4. Transprotection
  • 1.5. Mutual Protection
  • 1.6. Temporary Protection
  • 1.7. Protecting Groups As Not-So-Innocent Bystanders
  • 1.7.1. Neighbouring Group Participation
  • 1.7.2. Conformational and Electronic Effects
  • 1.7.3. Co-ordination Effects
  • 1.8. Protecting Groups and Solid-Phase Synthesis
  • 1.9. Reviews
  • 1.9.1. General Reviews on Protecting Groups
  • 1.9.2. Reviews on Enzyme-Labile Protecting Groups
  • 1.9.3. Reviews on Photo-Labile Protecting Groups
  • 1.9.4. Reviews on Linkers in Solid-Phase Synthesis
  • 1.9.5. Reviews on the Synthesis of Complex Targets Including Discussion of Protecting Group Problems and Strategies
  • References
  • Chapter 2. Carbonyl Protecting Groups
  • 2.1. Introduction
  • 2.2. O,O-Acetals
  • 2.2.1. Cyclic Acetals
  • 2.2.2. O,O-Acetals in Asymmetric Synthesis
  • 2.2.3. Acyclic O,O-Acetals
  • 2.3. S,S-Acetals
  • 2.4. O,S-Acetals
  • 2.5. N,O-Acetals
  • 2.6. Cyanohydrins
  • 2.7. Orthoester Derivatives
  • 2.7.1. O,O,O-Orthoesters
  • 2.7.2. O,S,S-Orthoesters
  • 2.7.3. S,S,S-Orthoesters
  • 2.8. Oxazolines
  • 2.9. Reviews
  • 2.9.1. Reviews Concerning the Preparation of O,O-Acetals and Their Use as Protecting Groups
  • 2.9.2. Reviews Concerning the Mechanism for Hydrolysis of Acetals
  • 2.9.3. Reviews Concerning O,O-Acetals as Reactive Functionality
  • 2.9.4. Reviews Concerning the Preparation, Chemistry, and Hydrolysis of O,S- and S,S-Acetals
  • 2.9.5. Reviews Concerning the Synthesis and Reactions of N,O-Acetals and Their Use in Asymmetric Synthesis
  • 2.9.6. Reviews Concerning the Chemistry of Orthoesters and Oxazolines
  • References
  • Chapter 3. Diol Protecting Groups
  • 3.1. Introduction
  • 3.2. O,O-Acetals
  • 3.2.1. Isopropylidene Acetals
  • 3.2.2. Cyclopentylidene and Cyclohexylidene Acetals
  • 3.2.3. The Arylmethylene Acetal Family
  • 3.2.4. Methylene Acetals
  • 3.2.5. Diphenylmethylene Acetals
  • 3.3. 1,2-Diacetals
  • 3.3.1. Dispoke Derivatives
  • 3.3.2. Cyclohexane-1,2-diacetals
  • 3.3.3. Butane-2,3-diacetals
  • 3.4. Silylene Derivatives
  • 3.5. 1,1,3,3-Tetraisopropyldisiloxanylidene Derivatives
  • 3.6. N,O-Acetals for the Protection of 1,2- and 1,3-Amino Alcohols
  • 3.7. Reviews
  • 3.7.1. Reviews Concerning the Protection of 1,2- and 1,3-Diols
  • 3.7.2. Reviews Concerning Acetal Derivatives of Carbohydrates
  • 3.7.3. Reviews Concerning 1,2-Diacetals
  • 3.7.4. Reviews Concerning N,O-Acetals
  • References
  • Chapter 4. Hydroxyl Protecting Groups
  • 4.1. Introduction
  • 4.2. Silyl Ethers
  • 4.2.1. Trimethylsilyl (TMS) Ethers
  • 4.2.2. Triethylsilyl (TES) Ethers
  • 4.2.3. tert-Butyldimethylsilyl (TBS) Ethers
  • 4.2.4. tert-Butyldiphenylsilyl (TBDPS) Ethers
  • 4.2.5. Triisopropylsilyl (TIPS) Ethers
  • 4.2.6. Diethylisopropylsilyl (DEIPS) Ethers
  • 4.2.7. Thexyldimethylsilyl (TDS) Ethers
  • 4.2.8. Triphenylsilyl (TPS) Ethers
  • 4.2.9. Di-tert-butylmethylsilyl (DTBMS) Ethers
  • 4.3. Alkyl Ethers
  • 4.3.1. Methyl Ethers
  • 4.3.2. tert-Butyl Ethers
  • 4.3.3. Benzyl Ethers (Bn)
  • 4.3.4. p-Methoxybenzyl (PMB) and 3,4-Di-methoxybenzyl (DMB) Ethers
  • 4.3.5. Trityl (Tr) Ethers
  • 4.3.6. Allyl Ethers and Allyloxycarbonyl Derivatives
  • 4.4. Alkoxymethyl Ethers
  • 4.4.1. Methoxymethyl (MOM) Ethers
  • 4.4.2. 2-Methoxyethoxymethyl (MEM) Ethers
  • 4.4.3. Benzyloxymethyl (BOM) and Related Ethers
  • 4.4.4. p-Methoxybenzyloxymethyl (PMBM) Ethers
  • 4.4.5. 2-(Trimethylsilyl)ethoxymethyl (SER) Ethers
  • 4.5. Tetrahydropyranyl (THP) and Related Ethers
  • 4.6. Methylthiomethyl (MTM) Ethers
  • 4.7. Esters
  • 4.7.1. Acetate Esters (Ac)
  • 4.7.2. Benzoate Esters (Bz)
  • 4.7.3. Pivalate Esters (R)
  • 4.7.4. Methoxyacetate Esters
  • 4.7.5. Chloroacetate Esters
  • 4.7.6. Levulinate Esters (Lev)
  • 4.8. Carbonates
  • 4.8.1. Benzyl Carbonates (RO-CBz)
  • 4.8.2. p-Nitrobenzyl Carbonates (RO-CO[subscript 2]PNB)
  • 4.8.3. tert-Butyl Carbonates (RO-Boc)
  • 4.8.4. 2,2,2-Trichloroethyl Carbonates (RO-Troc)
  • 4.8.5. 2-(Trimethylsilyl)ethyl Carbonates (RO-Teoc)
  • 4.8.6. Allyl Carbonates (RO-Aloc)
  • 4.9. Reviews
  • 4.9.1. General Reviews Concerning the Protection of Hydroxyls
  • 4.9.2. Reviews Concerning Enzyme-Mediated Esterification and Hydrolysis of Esters
  • 4.9.3. Reviews Concerning Organosilicon and Organotin Chemistry Relevant to Hydroxyl Protection
  • References
  • Chapter 5. Thiol Protecting Groups
  • 5.1. Introduction
  • 5.2. Thioether Derivatives
  • 5.2.1. tert-Butyl Thioethers
  • 5.2.2. Benzyl and Substituted Benzyl Thioethers
  • 5.2.3. Trityl (Tr) Thioethers
  • 5.2.4. 2-(Trimethylsilyl)ethyl (TMSE) Thioethers
  • 5.2.5. 2-Cyanoethyl Thioethers
  • 5.2.6. 9-Fluorenylmethyl (Fm) Thioethers
  • 5.3. Thiocarbonate Derivatives
  • 5.4. Disulfides as Protecting Groups and Targets
  • 5.5. Reviews
  • 5.5.1. Reviews Concerning the Protection of Thiols
  • 5.5.2. Reviews Concerning the Chemistry of Thiols and Disulfides
  • References
  • Chapter 6. Carboxyl Protecting Groups
  • 6.1. Introduction
  • 6.2. General Comments on the Esterification of Carboxylic Acids
  • 6.3. Methyl Esters and Derivatives
  • 6.3.1. Methyl Esters
  • 6.3.2. tert-Butyl Esters
  • 6.3.3. Benzyl Esters
  • 6.3.4. Allyl Esters
  • 6.3.5. Phenacyl Esters
  • 6.4. Alkoxyalkyl Esters
  • 6.5. Esters Cleaved by [beta]-Elimination Reactions
  • 6.5.1. 2,2,2-Trichloroethyl Esters
  • 6.5.2. 2-(Trimethylsilyl)ethyl (TMSE) Esters
  • 6.5.3. 2-Tosylethyl Esters and Related Base-Labile Groups
  • 6.6. Silyl Esters
  • 6.7. Reviews
  • 6.7.1. Reviews Concerning the Specific Use of Esters as Protecting Groups
  • 6.7.2. Reviews Concerning the Preparation of Esters
  • 6.7.3. Reviews Concerning Techniques for Facilitating Esterification
  • 6.7.4. Reviews Concerning the Use of Allyl Esters in Carboxyl Protection
  • 6.7.5. Reviews Concerning the Nucleophilic Cleavage of Esters
  • References
  • Chapter 7. Phosphate Protecting Groups
  • 7.1. Introduction
  • 7.2. The Reaction of Phosphate Esters with Nucleophiles
  • 7.3. Alkyl Esters
  • 7.3.1. Methyl and Isopropyl Esters
  • 7.3.2. tert-Butyl Esters
  • 7.3.3. Benzyl Esters
  • 7.3.4. Allyl Esters
  • 7.3.5. 3',5'-Dimethoxybenzoin Esters
  • 7.3.6. p-Hydroxyphenacyl Esters
  • 7.4. Esters Cleaved by [beta]-Elimination Reactions
  • 7.4.1. 2-Cyanoethyl Esters
  • 7.4.2. 9-Fluorenylmethyl Esters
  • 7.4.3. 2-(Trimethylsilyl)ethyl Esters
  • 7.4.4. 2-(Methylsulfonyl)ethyl Esters and Related Base-Labile Groups
  • 7.4.5. 2,2,2-Trichloroethyl Esters
  • 7.5. Reviews
  • 7.5.1. Reviews Concerning Protection for the Phosphate Group
  • 7.5.2. Reviews Concerning the Mechanism of Nucleophilic Substitution in Phosphate Esters
  • References
  • Chapter 8. Amino Protecting Groups
  • 8.1. Introduction
  • 8.2. Imides and Amides
  • 8.2.1. Phthaloyl (Phth) and Tetrachlorophthaloyl (TCP)
  • 8.2.2. Dithiasuccinyl (Dts)
  • 8.2.3. Trifluoroacetyl
  • 8.2.4. Relay Deprotection of N-Acyl Derivatives
  • 8.3. Carbamates
  • 8.3.1. Methoxy- and Ethoxycarbonyl
  • 8.3.2. tert-Butoxycarbonyl (Boc)
  • 8.3.3. Benzyloxycarbonyl (Z or Cbz)
  • 8.3.4. Allyloxycarbonyl (Aloc)
  • 8.3.5. 9-Fluorenylmethoxycarbonyl (Fmoc)
  • 8.3.6. 2-(Trimethylsilyl)ethoxycarbonyl (Teoc)
  • 8.3.7. 2,2,2-Trichloroethoxycarbonyl (Troc)
  • 8.4. Sulfonyl Derivatives
  • 8.4.1. Arylsulfonyl Derivatives
  • 8.4.2. 2-(Trimethylsilyl)ethylsulfonyl (SES) Derivatives
  • 8.5. N-Sulfenyl Derivatives
  • 8.6. N-Alkyl Derivatives
  • 8.6.1. N,O-Acetals
  • 8.6.2. Triazinanones
  • 8.6.3. Benzyl (Bn) and Diphenylmethyl (Dpm)
  • 8.6.4. Trityl (Tr) and 9-Phenylfluorenyl (PhFl)
  • 8.6.5. Allyl
  • 8.7. N-Silyl Derivatives
  • 8.8. Imine and Enamine Derivatives
  • 8.8.1. N-Bis(methylthio)methylene
  • 8.8.2. N-Diphenylmethylene
  • 8.9. Special Cases
  • 8.9.1. Orthogonal Protecting Groups for the Synthesis of Polyamines
  • 8.9.2. Protecting Groups for Guanidines
  • 8.9.3. Protecting Groups for Indoles, Pyrroles, and Imidazoles
  • 8.10. Reviews
  • 8.10.1. General Reviews on Amino Protecting Groups
  • 8.10.2. Reviews Concerning N-Protection in the Synthesis of [alpha]-Amino Aldehydes and Ketones
  • 8.10.3. Reviews Concerning N-Protection in the Synthesis of [beta]-Lactams
  • 8.10.4. Reviews Concerning N-Functional Groups Pertinent to Their Role as Protecting Groups
  • 8.10.5. Reviews Concerning the Synthesis of Natural Guanidine Derivatives
  • 8.10.6. Reviews Concerning the Synthesis of Natural Polyamines
  • References
  • Epilogue
  • Index
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