Greene's Protective Groups in Organic Synthesis
by Peter G. M. Wuts
6th Edition
Publisher: Wiley-Blackwell
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Book Details
| Print ISBN | 9781394233168 |
| eText ISBN | 9781394233182 |
| Publisher | Wiley-Blackwell |
| Publishing Year | 2025 |
| Edition | 6th Edition |
| Language | English |
| Pages | 1696 |
Greene's Protective Groups in Organic Synthesis, 6th Edition, provides a comprehensive reference guide for classifying, applying, and cleaving protective groups throughout complex organic syntheses. Authored by Peter G. M. Wuts, the work establishes systematic technical approaches for controlling chemical reactivity during multi-step reaction pathways.
The text details functional group protection and deprotection methodologies across key structural categories. Chapters systematically address protection for hydroxyl groups, including 12- and 13-diols, as well as phenols, catechols, carbonyl groups, and carboxyl groups. Further sections outline procedures for amino groups, thiol groups, and general protecting group formation.
This edition includes a new chapter examining how protective groups influence reactivity and selectivity within carbohydrate chemistry. The volume offers systematic guidance for complex multi-step organic synthesis.
Table of Contents
Chapter 1: The Role of Protective Groups in Organic Synthesis
- • Properties of a Protective Group
- • Historical Development
- • Development of New Protective Groups
- • Selection of a Protective Group from This Book
- • Synthesis of Complex Substances. Two Examples (As Used in the Synthesis of Himastatin and Palytoxin) of the Selection Introduction and Removal of Protective Groups
- • Synthesis of Himastatin
- • Synthesis of Palytoxin Carboxylic Acid
Chapter 2: Protection for the Hydroxyl Group Including 12- and 13- Diols
- • Ethers
- • Substituted Methyl Ethers
- • Substituted Ethyl Ethers
- • Methoxy- Substituted Benzyl Ethers
- • Silyl Ethers
- • Migration of Silyl Groups
- • Cleavage
- • Esters
- • Proximity Assisted Deprotection for Ester Cleavage
- • Miscellaneous Esters
- • Sulfonates Sulfenates and Sulfinates as Protective Groups for Alcohols
- • Carbonates
- • Carbamate Protection of Alcohols
- • Protection for 12- and 13- Diols
- • Monoprotection of Diols
- • Cyclic Acetals and Ketals
- • Chiral Ketones
- • Cyclic Ortho Esters
- • Silyl Derivatives
- • Cyclic Carbonates
- • Cyclic Boronates
Chapter 3: Protection for Phenols and Catechols
- • Protection for Phenols and Catechols
- • Ethers
- • Silyl Ethers
- • Esters
- • Carbonates
- • Carbamates
- • Phosphinates
- • Sulfonates
- • Protection for Catechols (12- Dihydroxybenzenes)
- • Cyclic Acetals and Ketals
- • Cyclic Esters
- • Protection for 2- Hydroxybenzenethiols
Chapter 4: Protection for the Carbonyl Group
- • Acetals and Ketals
- • Acyclic Acetals and Ketals
- • Cyclic Acetals and Ketals
- • Chiral Acetals and Ketals
- • Dithio Acetals and Ketals
- • Acyclic Dithio Acetals and Ketals
- • Cyclic Dithio Acetals and Ketals
- • Monothio Acetals and Ketals
- • Acyclic Monothio Acetals and Ketals
- • Cyclic Monothio Acetals and Ketals
- • Miscellaneous Derivatives
- • O- Substituted Cyanohydrins
- • Substituted Hydrazones
- • 12- Adducts to Aldehydes and Ketones
- • Protection of the Carbonyl Group as an Enolate Anions Enol Ethers Enamines and Imines
- • Lithium Diisopropylamide (LDA)
- • Monoprotection of Dicarbonyl Compounds
- • Selective Protection of α- and β- Diketones
- • Cyclic Ketals Monothio and Dithio Ketals
Chapter 5: Protection for the Carboxyl Group
- • Esters
- • General Preparations of Esters
- • General Cleavage of Esters
- • Transesterification
- • Enzymatically Cleavable Esters
- • Substituted Methyl Esters
- • 2- Substituted Ethyl Esters
- • Substituted Benzyl Esters
- • Silyl Esters
- • Activated Esters
- • Miscellaneous Derivatives
- • Stannyl Esters
- • Amides and Hydrazides
- • Amides
- • Protection of Sulfonic Acids
- • Protection of Boronic Acids
Chapter 6: Protection for the Thiol Group
- • Thioethers
- • S- Diphenylmethyl Substituted S- Diphenylmethyl and S- Triphenylmethyl Thioethers
- • 4- Methoxytrityl (Mtt–SR) Thioether
- • Substituted S- Methyl Derivatives: Monothio Dithio and Aminothio Acetals
- • Substituted S- Ethyl Derivatives
- • Silyl Thioethers
- • Thioesters
- • Thiocarbonate Derivatives
- • Thiocarbamate Derivatives
- • Miscellaneous Derivatives
- • Unsymmetrical Disulfides
- • Sulfenyl Derivatives
- • Protection for Dithiols: Dithio Acetals and Ketals
- • Protection for Sulfides
- • S–P Derivatives
- • Protection for the Amino Thiol Group
- • Protection for Selenols
Chapter 7: Protection for the Amino Group
- • Introduction to Amines
- • Carbamates
- • Substituted Ethyl Carbamates
- • Carbamates Cleaved by a 16- Elimination
- • Cleavage by β- Elimination
- • Photolytically Cleaved Carbamates
- • Miscellaneous Carbamates
- • Urea- Type Derivatives
- • Amides
- • Transamidation
- • Assisted Cleavage of Amides
- • Amide Cleavage Induced by Nitro Group Reduction
- • Amide Cleavage Induced by Release of an Alcohol
- • Amides Cleaved by Other Chemical Reactions
- • Bisprotection of Amines
- • Special –NH Protective Groups
- • N- Alkyl and N- Aryl Amines
- • Imine Derivatives
- • Enamine Derivatives
- • N- Heteroatom Derivatives
- • N- Metal Derivatives
- • N- N Derivatives
- • N- P Derivatives
- • N- Si Derivatives
- • N- S Derivatives
- • N- Sulfenyl Derivatives
- • Protection of Amino Alcohols
- • Protection for Imidazoles Pyrroles Indoles and Other Aromatic Heterocycles
- • N- Sulfonyl Derivatives
- • N- Alkyl and N- Aryl Derivatives
- • Amino Acetal Derivatives
- • Protection for the Amide ─NH
- • Protection for the Sulfonamide ─NH
Chapter 8: Protection for the Alkyne ─CH
Chapter 9: Protection for the Phosphate Group
- • Introduction
- • Some General Methods for Phosphate Ester Formation
- • Removal of Protective Groups from Phosphorus
- • Alkyl Phosphates
- • Phosphates Cleaved by Cyclodeesterification
- • 2- Substituted Ethyl Phosphates
- • Haloethyl Phosphates
- • Benzyl Phosphates
- • Phenyl Phosphates
- • Photochemically Cleaved Phosphate Protective Groups
- • Amidates
- • Miscellaneous Derivatives
Chapter 10: Protecting Group Effects in Carbohydrate Chemistry
- • Introduction
- • Early Observations Protecting Group- Induced Reactivity
- • Relative Reactivities
- • Fraser–Reid’s Concept of Armed and Disarmed
- • Examples of How Protecting Groups Arm and Disarm Glycosides
- • Aglycone Transfer
- • Participating Groups
- • Ester at the C- 2 Hydroxyl
- • Esters at Positions Other Than 2
- • Ethers Primarily at the C- 2 Hydroxyl
- • Conformational Restriction
- • Benzylidene Group and other Acetals
- • Directing Effect of Silylene Groups
- • Carbonates as Conformational Restrictors
- • Orthoester Conformational Restriction
- • Silyl Groups: Conformational and Reactivity Effect
- • Studies on the Conformational Flip Using Silyl Groups
- • Amino Sugar Protection
- • Imine Protection
- • Protection of the NH 2 as An Azide
- • Imide Protection
- • Oxazolidinones
- • Introduction to the Formation of Sialyl Glycosides
- • Amides and Their Effects
- • Protecting Group Effects in the Glycosylation of 2- Deoxy Sugars
- • Furanosides
- • Protecting Group Effects on Acceptors
- • C- Glycosylation
- • Sphingolipids
Chapter 11: Reactivities Reagents and Reactivity Charts
- • Reactivities
- • Reagents
- • Reactivity Charts
- • Reactivity Chart 1. Protection for Hydroxyl Group: Ethers
- • Reactivity Chart 2. Protection for Hydroxyl Group: Esters
- • Reactivity Chart 3. Protection for 12- and 13- Diols
- • Reactivity Chart 4. Protection for Phenols and Catechols
- • Reactivity Chart 5. Protection for the Carbonyl Group
- • Reactivity Chart 6. Protection for the Carboxyl Group
- • Reactivity Chart 7. Protection for the Thiol Group
- • Reactivity Chart 8. Protection for the Amino Group: Carbamates
- • Reactivity Chart 9. Protection for the Amino Group: Amides
- • Reactivity Chart 10. Protection for the Amino Group: Special ─NH Protective Groups
- • Reactivity Chart 11. Selective Deprotection of Silyl Ethers
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▶Research Sources (14)
- Greene's Protective Groups in Organic Synthesis
- Greene's Protective Groups in Organic Synthesis
- Greene's Protective Groups in Organic Synthesis
- Greene's protective groups in organic synthesis : Volume 1 - 2
- https://lernerbooks.com/products/search_results?se...
- Greene's Protective Groups in Organic Synthesis 6th Edition
- Getting Started Guide: Science: Books & Media
- Greene's Protective Groups in Organic Synthesis
- Book Review: Protective Groups in Organic Synthesis
- Greene's Protective Groups in Organic Synthesis - Ryefield Books
- Greene's Protective Groups in Organic Synthesis | Request PDF
- Protective groups in organic synthesis - SearchWorks catalog
- Greene's Protective Groups in Organic Synthesis, 2 Volume Set... - eBay UK
- Greene's Protective Groups in Organic Synthesis, 2 Volume Set - Booktopia
