DOI: 10.1055/b-003-108603
Kocieński, Philip J.: 2005

Protecting Groups

Print ISBN 9783131356031 · Online ISBN 9783131841735
More Information

Book

Editor: Kocieński, Philip J.

Title: Protecting Groups

Print ISBN: 9783131356031; Online ISBN: 9783131841735; Book DOI: 10.1055/b-003-108603

3rd Edition © 2005 Georg Thieme Verlag KG
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

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Front Matter
Chapter 1 Protecting Groups: An Overview
1.1 Death, Taxes, and Protecting Groups
1.2 Deprotection: The Concept of Orthogonal Sets
1.3 Relay Deprotection
1.4 Transprotection
1.5 Mutual Protection
1.6 Temporary Protection
1.7 Protecting Groups As Not-So-Innocent Bystanders
1.8 Protecting Groups and Solid-Phase Synthesis
1.9 Reviews
References
Chapter 2 Carbonyl Protecting Groups
2.1 Introduction
2.2 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
2.8 Oxazolines
2.9 Reviews
References
Chapter 3 Diol Protecting Groups
3.1 Introduction
3.2 O,O-Acetals (I)
3.2 O,O-Acetals (II)
3.3 1,2-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
References
Chapter 4 Hydroxyl Protecting Groups
4.1 Introduction
4.2 Silyl Ethers (I)
4.2 Silyl Ethers (II)
4.3 Alkyl Ethers (I)
4.3 Alkyl Ethers (II)
4.4 Alkoxymethyl Ethers (I)
4.4 Alkoxymethyl Ethers (II)
4.5 Tetrahydropyranyl (THP) and Related Ethers
4.6 Methylthiomethyl (MTM) Ethers
4.7 Esters
4.8 Carbonates
4.9 Reviews
References
Chapter 5 Thiol Protecting Groups
5.1 Introduction
5.2 Thioether Derivatives
5.3 Thiocarbonate Derivatives
5.4 Disulfides as Protecting Groups and Targets
5.5 Reviews
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 (I)
6.3 Methyl Esters and Derivatives (II)
6.4 Alkoxyalkyl Esters
6.5 Esters Cleaved by β-Elimination Reactions
6.6 Silyl Esters
6.7 Reviews
References
Chapter 7 Phosphate Protecting Groups
7.1 Introduction
7.2 The Reaction of Phosphate Esters with Nucleophiles
7.3 Alkyl Esters
7.4 Esters Cleaved by β-Elimination Reactions
7.5 Reviews
References
Chapter 8 Amino Protecting Groups
8.1 Introduction
8.2 Imides and Amides
8.3 Carbamates (I)
8.3 Carbamates (II)
8.4 Sulfonyl Derivatives
8.5 N-Sulfenyl Derivatives
8.6 N-Alkyl Derivatives
8.7 N-Silyl Derivatives
8.8 Imine and Enamine Derivatives
8.9 Special Cases
8.10 Reviews
References
Annex