Greene's protective groups in organic synthesis / / Peter G. M. Wuts

• Autore: Wuts Peter G. M.
• Pubblicazione: Hoboken, NJ : , : John Wiley & Sons, Incorporated, , [2025]; ©2025
• Edizione: 6th ed.
• Descrizione fisica: 1 online resource (1804 pages) : illustrations
• Disciplina: 547.2
• Soggetto topico: Protective groups (Chemistry); Organic compounds - Synthesis; Chemistry, Organic - Methodology; Chemistry Techniques, Synthetic; Organic Chemicals; Chemistry, Organic - methods
• Nota di contenuto: Cover -- Volume 1 -- Title Page -- Copyright Page -- Dedication -- Contents -- Preface -- Abbreviations -- 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 1,2- and 1,3-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 1,2-and 1,3-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 (1,2-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 -- 1,2-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 -and -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 -- Volume 2 -- Title Page -- Copyright Page -- Dedication -- Contents -- Preface -- Abbreviations -- Chapter 7 Protection for the Amino Group -- Introduction to Amines -- Carbamates -- Substituted Ethyl Carbamates -- Carbamates Cleaved by a 1,6-Elimination -- Cleavage by -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 -- Carbamates -- N-Alkyl and N-Aryl Derivatives -- Amino Acetal Derivatives -- Amides -- Protection for the Amide -NH -- Amides -- 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fs 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 NH2 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 -- Introduction -- 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 1,2-and 1,3-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 -- Index -- EULA.
• Sommario/riassunto: "Integral, reliable, and comprehensive guidance for chemists performing the complex syntheses required for the formation and cleavage of protective groups"--
• Altri titoli varianti: Protective groups in organic synthesis
• Titolo autorizzato: Greene's protective groups in organic synthesis
• ISBN: 9781394233182; 1394233183; 9781394233199; 1394233191; 9781394233175; 1394233175
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Lingua di pubblicazione: Inglese
• Record Nr.: 9911019677803321
• Lo trovi qui: Univ. Federico II