Greene's Protective Groups in Organic Synthesis, 2 Volume Set

Description

Integral, reliable, and comprehensive guidance for chemists performing the complex syntheses required for the formation and cleavage of protective groups. Organic synthesis is the preparation and creation of organic compounds for use in natural products, pharmaceuticals, and other molecules. The synthesis of molecules having multiple functional groups often requires the use of ‘protective groups’ to achieve site selectivity in a chemical reaction within a molecule bearing multiple sites of reactivity. Protective groups are installed temporarily to prevent unwanted reactions at a particular site, while transforming a different functional group. Once they have served their function, they are removed to expose the original group. Without a thorough understanding of the methods required to install and remove them, the design of a synthesis of a molecule having multiple functional groups in most cases is effectively impossible. Greene’s Protective Groups in Organic Synthesis, 6th Edition is the definitive compilation of protective groups, their classification, and their application in a wide array of situations. With a long tradition of comprehensive coverage, organized on the basis of the functional group in need of protection and subsequent deprotection, it is an essential reference and resource for all chemists involved in organic syntheses. Now fully updated to reflect the current state of the art, it remains an indispensable resource for generating life-changing organic products. This edition contains a new chapter on how protective groups effect reactivity and selectivity in carbohydrate chemistry. Readers of the sixth edition of Greene’s Protective Groups in Organic Synthesis will also find: Methodology for planning selectivity in organic syntheses. Detailed discussion of all major functional groups including ethers, amides, and phenols. A discussion of the impact of protective groups on reactivity in carbohydrates. Greene’s Protective Groups in Organic Synthesis is ideal for synthetic organic chemists or medicinal chemists in academia, industry ― pharmaceuticals, food, agrochemicals, and biotech ― or government agencies. Volume 1 Cover Half Title Greene's Protective Groups in Organic Synthesis: Volume 1 Copyright Dedication Contents Volume 1 Volume 2 Preface Abbreviations Protective Groups Abbreviations Reagents 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 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 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 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 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 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 Cover Half Title Greene's Protective Groups in Organic Synthesis: Volume 2 Copyright Dedication Contents Volume 1 Volume 2 Preface Abbreviations Protective Groups Abbreviations Reagents 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 8. Protection for the Alkyne -CH 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 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 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